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(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE structure

CAS No.: 77943-39-6

Chemical Name:: (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

Synonyms: (4R,5S)-4-Methyl-5-phenyloxazolidin-2-one;(4S,5S)-4-Methyl-5-phenyloxazolidin-2-one;TB-2039;4-methyl-5-phenyl-2-oxazolidinone;5β-Phenyl-4β-methyloxazolidine-2-one;4α-Methyl-5α-phenyloxazolidine-2-one;4-Methyl-5-phenyl-1,3-oxazolidin-2-one;(4R-5S)-4-Methyl-5-Phenyl-2-Oxazocidin;(4R,5S)-4-Methyl-5-phenyl-2-oxazolidone;(4R,5S)-4-Methyl-4-phenyl-2-oxazolidone

CBNumber:: CB5321737

Molecular Formula:: C10H11NO2

Molecular Weight:: 177.2

MDL Number:: MFCD00010845

MOL File:: 77943-39-6.mol

MSDS File:: SDS

Last updated:2023-05-25 10:25:51

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(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Properties

Melting point	121-123 °C(lit.)
Boiling point	309.12°C (rough estimate)
Density	1.1607 (rough estimate)
refractive index	1.5168 (estimate)
storage temp.	Sealed in dry,Room Temperature
solubility	Chloroform (Slightly), Ethyl Acetate (Slightly)
form	Liquid
pka	12.35±0.60(Predicted)
color	Clear colorless to yellow-brown, may darken in storage
optical activity	[α]18/D +168°, c = 2 in chloroform
BRN	1211705
InChI	InChI=1S/C10H11NO2/c1-7-9(13-10(12)11-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H,11,12)/t7-,9-/m1/s1
InChIKey	PPIBJOQGAJBQDF-VXNVDRBHSA-N
SMILES	O1[C@@H](C2=CC=CC=C2)[C@@H](C)NC1=O
CAS DataBase Reference	77943-39-6(CAS DataBase Reference)
FDA UNII	05339K0T1Y

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H315-H319-H335
Precautionary statements	P261-P305+P351+P338
Hazard Codes	N
Safety Statements	22-24/25
WGK Germany	3
HS Code	29349990

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE price More Price(19)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	298891	(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone 99%	77943-39-6	5g	$103	2024-03-01	Buy
TRC	M325455	(4R,5S)-4-Methyl-5-phenyloxazolidinone	77943-39-6	100mg	$165	2021-12-16	Buy
AK Scientific	2222AC	(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone	77943-39-6	5g	$184	2021-12-16	Buy
Matrix Scientific	121366	(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone 98%	77943-39-6	5g	$192	2021-12-16	Buy
SynQuest Laboratories	4H56-1-572	(4R,5S)-4-Methyl-5-phenyl-2-oxazolidone 97%	77943-39-6	5G	$125	2021-12-16	Buy

Product number	Packaging	Price	Buy
298891	5g	$103	Buy
M325455	100mg	$165	Buy
2222AC	5g	$184	Buy
121366	5g	$192	Buy
4H56-1-572	5G	$125	Buy

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Chemical Properties,Uses,Production

Chemical Properties

white to light yellow crystal powde

Uses

Evan′s chiral auxiliary (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone reacts with carboxylic acids to produce corresponding acyl derivatives in the presence of a diisopropylcarbodiimide reagent. It can also employed in the preparation of N-sulfinyloxazolidinone reagent (chiral sulfinyl transfer reagent), which reacts with nucleophiles such as Grignard reagents, enolates, and metalated amides to produce the chiral sulfoxides, sulfinate esters, and sulfonamides.

Uses

(4R,5S)-4-Methyl-5-phenyloxazolidinone is used as effective chiral auxiliary for conjugate addition asymmetric synthesis of (-)-aplysillamide B.

Preparation

To a solution of (1S,2R)-norephedrine (40 g, 0.26 mol) in toluene (400 mL) was added diethyl carbonate (37 mL, 0.32 mol). The mixture was heated to reflux (under Ar) while 40 mL of solvent was removed through the use of a Dean–Stark apparatus. The mixture was allowed to cool for 20 min, and then sodium methoxide (1 g) was added. Upon reheating, an EtOH/toluene azeotropic mixture was removed at 75–77 °C. After 3 h, the reaction was complete and the temperature of the mixture had increased to 125 °C. The mixture was left to stand at room temperature for 16 h, whereupon (4R,5S)-4-methyl-5-phenyloxazolidin-2-one (40.6 g) crystallized and could be collected. The solvent was removed from the filtrate in vacuo and the residue was redissolved in EtOAc (250 mL). This solution was washed with brine (50 mL) and a precipitate was removed by filtration. The solvent was then removed in vacuo and toluene (50 mL) was added to the residue. Removal of the toluene by distillation yielded oily crystals of the oxazolidinone, which were washed with Et2O to afford 4.5 g (total 45 g, 97%).

Definition

ChEBI: (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone is a member of benzenes.

Preparation

A mechanically stirred mixture of (1S,2R)-norephedrine 710 (151 g, 1.00 mol) ([α]589 =+ 33.4 (c= 7, water)), as the hydrochloride salt, diphenyl carbonate (236 g, 1.10 mol), and anhydrous potassium carbonate (152 g, 1.10 mol) was heated at 110 °C for 4–6 h. The resultant mixture was then cooled to <60 °C. Excess diphenyl carbonate was hydrolyzed by adding methanol (600 mL) and heating the mixture under reflux for 0.5 h. Sufficient water (400–600 mL) was then added to dissolve the potassium carbonate. Methanol was removed in vacuo. The product and phenol were extracted into dichloromethane (3 × 1 L). The combined extracts were washed with 2 m aqueous sodium hydroxide (3 × 1 L) to remove the phenol, 1 m aqueous hydrochloric acid (1 × 1 L), and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give 195 g (110% mass balance) of a light-yellow solid. Recrystallization from toluene (600 mL) afforded 145–165 g (82–93%) of oxazolidinone 711 as a white crystalline solid.
the preparation of (4R,5S)-4-Methyl-5-phenyl-2-oxazolidinone

Synthesis Reference(s)

Tetrahedron Letters, 40, p. 6059, 1999 DOI: 10.1016/S0040-4039(99)01256-3

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Preparation Products And Raw materials

Raw materials

Preparation Products

N-CROTONYL-(4R,5S)-4-METHYL 5-PHENYL-2-OXAZOLIDINONE

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Suppliers

Global( 136)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Henan Bao Enluo International TradeCo.，LTD	+86-17331933971 +86-17331933971	deasea125996@gmail.com	China	2503	58
Capot Chemical Co.,Ltd.	571-85586718 +8613336195806	sales@capotchem.com	China	29797	60
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	32480	60
career henan chemical co	+86-0371-86658258	sales@coreychem.com	China	29914	58
Jinan Carbotang Biotech Co.,Ltd.	+8615866703830	figo.gao@foxmail.com	China	6992	58
Accela ChemBio Inc.	(+1)-858-699-3322	info@accelachem.com	United States	19965	58
Hubei xin bonus chemical co. LTD	86-13657291602	linda@hubeijusheng.com	CHINA	22968	58
Alchem Pharmtech,Inc.	8485655694	sales@alchempharmtech.com	United States	63711	58
Dideu Industries Group Limited	+86-29-89586680 +86-15129568250	1026@dideu.com	China	29220	58
Dayang Chem (Hangzhou) Co.,Ltd.	571-88938639 +8617705817739	info@dycnchem.com	CHINA	52867	58

Supplier	Advantage
Henan Bao Enluo International TradeCo.，LTD	58
Capot Chemical Co.,Ltd.	60
ATK CHEMICAL COMPANY LIMITED	60
career henan chemical co	58
Jinan Carbotang Biotech Co.,Ltd.	58
Accela ChemBio Inc.	58
Hubei xin bonus chemical co. LTD	58
Alchem Pharmtech,Inc.	58
Dideu Industries Group Limited	58
Dayang Chem (Hangzhou) Co.,Ltd.	58

View Lastest Price from (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2023-05-27	(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE 77943-39-6	US $150.00 / kg	1kg	99.9%	10000MT	Henan Bao Enluo International TradeCo.，LTD
2023-05-27	4R,5S)-4-Methyl-5-phenyl-1,3-oxazolidin-2-one 77943-39-6	US $30.00 / kg	1kg	99.9%	10000MT	Henan Bao Enluo International TradeCo.，LTD
2021-07-02	(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone 77943-39-6	US $15.00-10.00 / KG	1KG	99%+ HPLC	Monthly supply of 1 ton	Zhuozhou Wenxi import and Export Co., Ltd

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE
77943-39-6
US $150.00 / kg
99.9%
Henan Bao Enluo International TradeCo.，LTD

4R,5S)-4-Methyl-5-phenyl-1,3-oxazolidin-2-one
77943-39-6
US $30.00 / kg
99.9%
Henan Bao Enluo International TradeCo.，LTD

(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone
77943-39-6
US $15.00-10.00 / KG
99%+ HPLC
Zhuozhou Wenxi import and Export Co., Ltd

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Spectrum

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE(77943-39-6)¹HNMR (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE(77943-39-6)IR (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE(77943-39-6)FT-IR (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE(77943-39-6)Raman

77943-39-6((4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE)Related Search:

(R)-(+)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE (R)-4,5,5-TRIPHENYL-2-OXAZOLIDINONE (R)-(+)-5,5-DIPHENYL-4-BENZYL-2-OXAZOLIDINONE (4S,5R)-(-)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

Oxazole 2-Oxazolidone N-ACETYL-(4S,5R)-4-METHYL 5-PHENYL-2-OXAZOLIDINONE (2R,4S)-3-Benzoyl-4-methyl-2-phenyl-5-oxazolidinone N-CROTONYL-(4S,5R)-4-METHYL 5-PHENYL-2-OXAZOLIDINONE,N-CROTONYL-(4S,5R)-4-METHYL 5-PHENYL-2-OXAZOLIDINONE

(R)-(+)-5,5-DIPHENYL-4-METHYL-2-OXAZOLIDINONE (4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone ,(4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone (4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone ,(4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone N-PROPIONYL-(4S,5R)-4-METHYL- 5-PHENYL-2-OXAZOLIDINONE (R)-(+)-5,5-DIPHENYL-4-ISOBUTYL-2-OXAZOLIDINONE

(4R,5S)-(+)-CIS-4,5-DIPHENYL-2-OXAZOLIDINONE N-CROTONYL-(4R,5S)-4-METHYL 5-PHENYL-2-OXAZOLIDINONE,N-CROTONYL-(4R,5S)-4-METHYL 5-PHENYL-2-OXAZOLIDINONE (2S,4R)-3-Benzoyl-4-methyl-2-phenyl-5-oxazolidinone

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(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone 99% 4-Methyl-5-phenyl-1,3-oxazolidin-2-one (4R,5S)-(-)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE (4R,5S)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE (4R,5S)-4-Methyl-5-phenyl-2-oxazolidone (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLID -INONE, 99% (99% EE/GLC) (4R,5S)-4-METHYL-5-PHENYL-2-OXAZOLIDI DI NONE 2-Oxazolidinone, 4-methyl-5-phenyl-, (4R,5S)- 4-methyl-5-phenyl-2-oxazolidinone (4S)-4β-Methyl-5α-phenyloxazolidine-2-one 5β-Phenyl-4β-methyloxazolidine-2-one (4R)-4α-Methyl-5α-phenyloxazolidin-2-one 4α-Methyl-5α-phenyloxazolidine-2-one (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone,99% (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidine (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone ,98% (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE USP/EP/BP (4R,5S)-4-Methyl-5-phenyl-1,3-oxazolidin-2-one (4S,5S)-4-Methyl-5-phenyloxazolidin-2-one (4R,5S)-4-Methyl-5-phenyloxazolidin-2-one TB-2039 (4R-5S)-4-Methyl-5-Phenyl-2-Oxazocidin (4R,5S)-4-Methyl-4-phenyl-2-oxazolidone 77943-39-6 Chiral Auxiliaries Asymmetric Synthesis Oxazolidinone Derivatives chiral Peptide