Ammonium Chloride → HCID 178525194, compound

HRID 846940Notes

Reaction equation

HRID 846940 reaction equation
[C:1]([C@@H:3]1[CH2:7][C@H:6]([S:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][N:4]1[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)=[O:29])#[N:2].[N-:41]=[N+:42]=[N-:43].[Na+].[Cl-].[NH4+]>CN(C)C=O>[N+:38]([C:35]1[CH:36]=[CH:37][C:32]([CH2:31][O:30][C:28]([N:4]2[CH2:5][C@@H:6]([S:8][C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:7][C@H:3]2[C:1]2[NH:43][N:42]=[N:41][N:2]=2)=[O:29])=[CH:33][CH:34]=1)([O-:40])=[O:39]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 53487023(4-Nitrophenyl)methyl (2S,4S)-2-cyano-4-[(triphenylmethyl)sulfanyl]pyrrolidine-1-carboxylate

Product 1

HCID 178525194HCID 178525194, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2S,4S)-2-cyano-1-(4-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine (2.00 g) and sodium azide (0.30 g) in dimethylformamide (20 ml) was stirred at 110°-120° C. for 9 hours in the presence of ammonium chloride (0.05 g). The mixture was concentrated under reduced pressure to give a residue. The residue was subjected to a column chromatography on silica gel (20 g) and eluted with a mixture of acetone and chloroform (10:90, V/V) to give (2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-(1H-tetrazol-5-yl)-4-tritylthiopyrrolidine (1.86 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a residue
  3. washeluted with a mixture of acetone and chloroform (10:90, V/V)

Sources & evidence

ORD record
ord-e922efd839ca41f4b1d504fce62114be
Source dataset
uspto-grants-1992_08
Patent number
US05138064

Reaction notes

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