Sodium Azide → (2S,4S)-4-acetylthio-2-(4-azidomethylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 846954Notes

Reaction equation

[C:1]([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[S:24][CH:25]=[C:26]([CH2:28]OS(C)(=O)=O)[N:27]=2)[CH2:6]1)(=[O:3])[CH3:2].[N-:34]=[N+:35]=[N-:36].[Na+]>CN(C)C=O>[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)=[O:11])[C@H:7]([C:23]2[S:24][CH:25]=[C:26]([CH2:28][N:34]=[N+:35]=[N-:36])[N:27]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a soluiton of (2S,4S)-4-acetylthio-2-[4-(methanesulfonyloxymethyl)thiazol-2-yl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.5 g) in dimethylformamide (20 ml) was added sodium azide (0.15 g) at ambient temperature. After stirring at 70° C. for 2 hours, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine successively, dried over magnesium sulfate and concentrated to give a syrup. The syrup was subjected to a column chromatography on silica gel and eluted with a mixture of acetone and dichloromethane (1:9, V/V) to give (2S,4S)-4-acetylthio-2-(4-azidomethylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (500 mg).

Workup

customthe mixture was partitioned between ethyl acetate and water
washThe organic layer was washed with water and brine successively
dry with materialdried over magnesium sulfate
concentrationconcentrated
customto give a syrup
washeluted with a mixture of acetone and dichloromethane (1:9, V/V)

Sources & evidence

ORD record: ord-d6e3ef34e56b47e1beb1e519ffa2a471
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05138064

Reaction notes

Loading…