| Identification | Back Directory | [Name]
(S)-1-Benzyl 2-Methyl 4-Oxopyrrolidine-1,2-Dicarboxylate | [CAS]
16217-15-5 | [Synonyms]
Z-4-Oxo-Pro-OMe
CBZ-4-Oxo-Pro-OMe
1-Cbz-4-oxo-L-proline methyl ester
(S)-Cbz 1-methyl-4-oxopyrrolidine-2-carboxylate
1-benzyloxycarbonyl-4-oxo-L-proline methyl ester
(S)-1-Benzyloxycarbonyl-4-oxoproline methyl ester
1-benzyloxycarbonyl-4-keto-(S)-proline Methyl ester
1-benzyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate
（s）-L-benzyl 2-methyl 4-oxopyrrolidine-1，2-dicarboxyl
（s）-L-benzyl-2-methyl 4-oxopyrrolidine-1，2-dicarboxylate
(S)-1-Benzyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate
1-Benzyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate
O1-Benzyl O2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate
1-O-benzyl 2-O-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate
(S)-1-Benzyl 2-Methyl 4-Oxopyrrolidine-1,2-Dicarboxylate USP/EP/BP
(2S)-4-Oxo-1,2-pyrrolidinedicarboxylic Acid 1-Benzyl 2-Methyl Ester
(2S)-4-oxo-1,2-Pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester
1,2-Pyrrolidinedicarboxylic acid, 4-oxo-, 2-methyl 1-(phenylmethyl) ester, (2S)- | [Molecular Formula]
C14H15NO5 | [MDL Number]
MFCD09608116 | [MOL File]
16217-15-5.mol | [Molecular Weight]
277.27 |
| Chemical Properties | Back Directory | [Boiling point ]
422.1±45.0 °C(Predicted) | [density ]
1.306±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform, Dichloromethane, Dimethylsulfoxide, Ethyl Acetate | [form ]
Oil | [pka]
-3.91±0.40(Predicted) | [color ]
Light Yellow |
| Hazard Information | Back Directory | [Chemical Properties]
Light Yellow Oil | [Uses]
(S)-1-Benzyl 2-Methyl 4-Oxopyrrolidine-1,2-Dicarboxylate is used in the preparation of dipeptidyl peptidase IV inhibitors and (hydroxy)(carbamoyl)pyrimidinones as potent and orally bioavailable HIV integrase inhibitors.
| [Synthesis]
General procedure for the synthesis of N-Cbz-4-oxo-L-proline methyl ester from (2S,4S)-N-CBZ-4-hydroxyproline methyl ester: Dess-Martin periodinane (3.0 g, 7.1 mmol) was added batchwise to a solution of compound (2S,4S)-N-CBZ-4-hydroxyproline methyl ester (1.0 g , 3.6 mmol) in a solution of dichloromethane (DCM, 20 mL). After addition, the reaction mixture was stirred at room temperature for 1.0 hour. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, v/v=5/1) to afford N-Cbz-4-oxo-L-proline methyl ester as a yellow oil (0.79 g, 79.5% yield). The structure of the compound was confirmed by the following spectral data: 1H NMR (400 MHz, CDCl3) δ (ppm): 7.47 (d, 2H, J=8.24 Hz), 7.38 (d, 2H, J=8.24 Hz), 7.24 (m, 1H), 5.09 (s, 2H), 4.18 (t, 1H), 3.68 (s, 3H). 3.38 (m, 1H), 3.32 (m, 1H), 2.21 (m, 1H), 1.96 (m, 1H). | [References]
[1] Patent: WO2014/82380, 2014, A1. Location in patent: Paragraph 00510; 00513
[2] Patent: EP2730572, 2014, A1. Location in patent: Paragraph 0706-0716
[3] Patent: EP2730572, 2015, B1. Location in patent: Paragraph 0706-0716
[4] Patent: WO2014/131315, 2014, A1. Location in patent: Page/Page column 176
[5] Patent: EP2730572, 2015, B1. Location in patent: Paragraph 0700; 0708 |
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