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

HRID 37279
Notes
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Reaction equation

HRID 37279 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 57163868(2S,4S)-4-acetylthio-2-[4-(methanesulfonyloxymethyl)thiazol-2-yl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 18638814(2S,4S)-4-acetylthio-2-(4-azidomethylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 46.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution 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

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

Sources & evidence

ORD record
ord-b51de1a44ac1446da55257530c0fb4f3
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05420122

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes