ChemicalBook--->CAS DataBase List--->149597-92-2

149597-92-2

149597-92-2 Structure

149597-92-2 Structure
IdentificationMore
[Name]

3,3-Diphenyl-L-alanine
[CAS]

149597-92-2
[Synonyms]

3,3-DIPHENYL-L-ALANINE
BETA-PHENYL-L-PHENYLALANINE
H-(3-PHENYL)PHE-OH
H-ALA(3,3-DIPHENYL)-OH
H-DPH-OH
L-3,3-DIPHENYLALANINE
RARECHEM BK PT 0193
(S)-2-AMINO-3,3-DIPHENYL-PROPIONIC ACID
(S)-DIPHENYLALANINE
L-DiPhenylalanine
beta-Phenyl-L-phenylalanin
H-L-Dip-OH
β-Phenyl-L-phenylalanine, (S)-2-Amino-3,3-diphenylpropionic acid
L-3,3-Diphenyl-Ala-OH
[Molecular Formula]

C15H15NO2
[MDL Number]

MFCD01631989
[Molecular Weight]

241.29
[MOL File]

149597-92-2.mol
Chemical PropertiesBack Directory
[Melting point ]

234-240 °C
[Boiling point ]

389.2±30.0 °C(Predicted)
[density ]

1.198±0.06 g/cm3(Predicted)
[storage temp. ]

Store at 0°C
[form ]

solid
[pka]

2.11±0.10(Predicted)
[color ]

White
[Major Application]

peptide synthesis
[InChI]

InChI=1/C15H15NO2/c16-14(15(17)18)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13-14H,16H2,(H,17,18)/t14-/s3
[InChIKey]

PECGVEGMRUZOML-AWEZNQCLSA-N
[SMILES]

C([C@H](N)C(=O)O)(C1=CC=CC=C1)C1=CC=CC=C1 |&1:1,r|
[CAS DataBase Reference]

149597-92-2(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

T,Xi
[Risk Statements ]

R25:Toxic if swallowed.
[Safety Statements ]

S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[RIDADR ]

UN 2811 6.1/PG 3
[WGK Germany ]

2
[HazardClass ]

6.1
[PackingGroup ]

Ⅲ
[HS Code ]

2922498590
[Storage Class]

6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials
[Hazard Classifications]

Acute Tox. 2 Oral
Hazard InformationBack Directory
[Chemical Properties]

White powder
[Uses]

3,3-Diphenyl-L-alanine is used as organic chemical synthesis intermediate.
[reaction suitability]

reaction type: solution phase peptide synthesis
[Synthesis]

1-Imidazolidinecarboxylic acid, 2-(2,6-dichlorophenyl)-4-(diphenylmethyl)-5-oxo-3-[(1R)-1-phenylethyl]-, 1,1-dimethylethyl ester, (2R,4S)-

1004755-24-1

3,3-Diphenyl-L-alanine

149597-92-2

Step 2: 1,1-dimethylethyl-(2R)-(2,6-dichlorophenyl)-(4S)-(diphenylmethyl)-5-oxo-3-((1'R)-phenylethyl)tetrahydro-1H-1-imidazolecarboxylate (188 mg, 0.31 mmol) was dissolved in a solvent mixture of 7.5 mL of tetrahydrofuran and 1 mL of 1 M hydrochloric acid, and the atmosphere of the reaction vessel was replaced with nitrogen. . To the mixture was added 90 mg of 20% palladium-carbon hydroxide catalyst; the atmosphere was again replaced with nitrogen and then hydrogen. After 100 hours of reaction at room temperature and 2.2 MPa hydrogen pressure, the catalyst was separated by filtration. The resulting product was washed once with 5 mL of tetrahydrofuran and 3 mL of distilled water, respectively, and the solvent was removed under reduced pressure. To the mixture was added 7.5 mL of 6M hydrochloric acid; the mixture was heated and refluxed at an external temperature of 120-130°C for 2.5 hours. Thereafter, the reaction mixture was cooled to an external temperature of 0°C. After adjusting the pH to 6 to 7 by adding 30% aqueous sodium hydroxide solution thereto, the solvent was removed under reduced pressure. The amount of (S)-2-amino-3,3-diphenylpropionic acid contained in the residue was determined under the following analytical conditions. As a result, the yield was 76% and the ee value was 95.7%.

[References]

[1] Patent: EP2050738, 2009, A1. Location in patent: Page/Page column 39-40
Spectrum DetailBack Directory
[Spectrum Detail]

3,3-Diphenyl-L-alanine(149597-92-2)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

149597-92-2(sigmaaldrich)
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