| Identification | More | [Name]
(S)-(-)-3-TERT-BUTOXYCARBONYL-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE | [CAS]
108149-60-6 | [Synonyms]
2,2-DIMETHYL OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER 4-METHYL ESTER
3-(1,1-DIMETHYLETHYL)-4-METHYL-(S)-2,2-DIMETHYL-3,4-OXAZOLIDINE CARBOXYLATE
3-(1,1-DIMETHYLETHYL)-4-METHYL-(S)-2,2-DIMETHYL-3,4-OXAZOLIDINEDICARBOXYLATE
BOC-2,2-DIMETHYLOXAZOLIDINE-4-CARBOXYLIC ACID METHYL ESTER
METHYL 3-(TERT-BUTOXYCARBONYL)-2, 2-DIMETHYL-4-OXAZOLIDINECARBOXYLATE
METHYL (S)-(-)-3-TERT-BUTOXYCARBONYL-2,2-DIMETHYL-4-OXAZOLIDINECARBOXYLATE
METHYL (S)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYL-4-OXAZOLIDINECARBOXYLATE
(S)-(-)-3-BOC-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE
(S)-(-)-3-TERT-BUTOXYCARBONYL-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE
(S)-N-BOC-2,2-DIMETHYLOXAZOLINDINE-4-CARBOXYLIC ACID METHYL ESTER
Methyl (S)-(-)-3-Boc-2,2-dimethyl-4-oxazolidinecarboxylate, 98% (99% ee)
methyl(s)-3-(t-butoxycarbonyl)-2,2-di-me-4-oxazolidinecarboxylate(ee)
methyl (s)-(-)-3-boc-2,2-dimethyl-4-oxazolidinecarboxylate
(S)-(-)-3-tert-Butoxycarbonyl-4-methoxycarbonyl-
TERT-BUTYL METHYL (4S)-2,2-DIMETHYLOXAZOLIDINE-3,4-DICARBOXYLATE
3-(1,1-dimethylethyl)-4-methyl-(S)-2,2-dimethyl-3,4-oxazolidinedicarboxylate, 98 %
methyl (tert-butoxycarbonyl)dimethyloxazolidinecarboxylate
METHYL-(S)-3-(TERT.-BUTOXYCARBONYL)-2,2-DIMETHYL-4-OXAZOLIDINECARBOXYLATE, TECH.,93%
Methyl-(S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate, tech.
Methyl (4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylate | [Molecular Formula]
C12H21NO5 | [MDL Number]
MFCD00192279 | [Molecular Weight]
259.3 | [MOL File]
108149-60-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear yellow liquid | [Boiling point ]
101-102 °C2 mm Hg(lit.) | [density ]
1.082 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.443(lit.)
| [Fp ]
199 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Liquid | [pka]
-3.58±0.60(Predicted) | [color ]
Clear yellow | [Optical Rotation]
[α]20/D 55°, c = 1.3 in chloroform | [InChI]
1S/C12H21NO5/c1-11(2,3)18-10(15)13-8(9(14)16-6)7-17-12(13,4)5/h8H,7H2,1-6H3/t8-/m0/s1 | [InChIKey]
ZNBUXTFASGDVCL-QMMMGPOBSA-N | [SMILES]
COC(=O)[C@@H]1COC(C)(C)N1C(=O)OC(C)(C)C | [CAS DataBase Reference]
108149-60-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
NA 1993 / PGIII | [WGK Germany ]
3
| [HS Code ]
29349990 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear yellow liquid | [Uses]
(S)-(-)-3-tert-Butoxycarbonyl-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine is a useful intermediate used in the improved synthesis of Garner′s aldehyde and analogs with multiple pharmaceutical applications. | [Synthesis]
To a solution of Boc-L-serine methyl ester (2a, 1.94 g, 8.85 mmol, 1.00 eq.) in dichloromethane (20.0 mL) was added 2,2-dimethoxypropane (3.25 mL, 26.6 mmol, 3.00 eq.) and boron trifluoride-ether complex (0.0553 mL, 0.443 mmol, 0.500 equivalent) in a dilute solution in dichloromethane (15.0 mL). The reaction mixture was stirred at 25 °C for 3 h and then quenched with saturated aqueous NaHCO3 solution. The aqueous layer was extracted with two portions of ethyl acetate. The combined organic layers were washed with 10% NaCl aqueous solution, dried with Na2SO4, filtered, and concentrated in vacuum. Purification of the residue by silica gel column chromatography (16% hexane solution of ethyl acetate) afforded (R)-(-)-3-BOC-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine (2.28 g, 8.79 mmol, 99%) as a colorless oil. | [References]
[1] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 106 - 110
[2] Tetrahedron Letters, 1999, vol. 40, # 1, p. 113 - 116
[3] European Journal of Organic Chemistry, 2017, vol. 2017, # 6, p. 1045 - 1051
[4] Patent: WO2015/156601, 2015, A1. Location in patent: Page/Page column 23; 24; 25
[5] Organic Letters, 2003, vol. 5, # 23, p. 4253 - 4256 |
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