Acetic Acid → (2S,4S)-2-(2-aminothiazol-4-yl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 1649807Notes

Reaction equation

C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([C:23]2[N:24]=[C:25]([NH2:28])[S:26][CH:27]=2)[CH2:6]1)(=O)C.C[O-].[Na+].C(O)(=O)C>CO.ClCCl>[NH2:28][C:25]1[S:26][CH:27]=[C:23]([C@@H:7]2[CH2:6][C@H:5]([SH:4])[CH2:9][N:8]2[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[N:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2S,4S)-4-acetylthio-(2-aminothiazol-4-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.26 g) in a mixture of methanol (20 ml) and dichloromethane (10 ml) was added sodium methoxide (28% solution in methanol, 1.2 ml) at -30° to -20° C. under an atmosphere of nitrogen. After stirring at 0° C. for 1 hour, acetic acid (0.36 ml) was added to the mixture. The solution was evaporated under reduced pressure, then the residue was dissolved in ethyl acetate, and washed with water, saturated aqueous sodium bicarbonate and brine successively. The dried organic layer was evaporated to give (2S,4S)-2-(2-aminothiazol-4-yl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.13 g).

Workup

customThe solution was evaporated under reduced pressure
dissolutionthe residue was dissolved in ethyl acetate
washwashed with water, saturated aqueous sodium bicarbonate and brine successively
customThe dried organic layer was evaporated

Sources & evidence

ORD record: ord-4d1fca566f0c42cc8ef3fa37e2f7b790
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04921852

Reaction notes

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