Sodium Azide → HCID 131716380, compound

HRID 1590476Notes

Reaction equation

HRID 1590476 reaction equation
CS(O[N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C@@H:13]2[CH2:17][C@H:16]([S:18][C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][N:14]2[C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=2)=[O:39])[CH2:8][CH2:7]1)(=O)=O.[N-:51]=[N+:52]=[N-:53].[Na+]>CN(C)C=O>[N:51]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C@@H:13]2[CH2:17][C@H:16]([S:18][C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][N:14]2[C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=2)=[O:39])[CH2:8][CH2:7]1)=[N+:52]=[N-:53]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 131716378HCID 131716378, compound

Product 1

HCID 131716380HCID 131716380, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2S,4S)-2-[(4-methanesulfonyloxypiperizin-1-yl)methyl]-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (4.38 g) and sodium azide (1.19 g) in N,N-dimethylformamide (40 ml) was stirred at 90°-100° C. for 2 hours. The reaction mixture was poured into ice-water (300 ml) and extracted 3 times with saturated aqueous sodium chloride, dried over magnesium sulfate, and evaporated in vacuo. The resulting residue was chromatographed on silica gel (150 g) eluting with a mixture of dichloromethane and acetone (10:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-2-[(4-azidopiperizin-1-yl)methyl]-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (2.51 g).

Workup

  1. extractionextracted 3 times with saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe resulting residue was chromatographed on silica gel (150 g)
  5. washeluting with a mixture of dichloromethane and acetone (10:1 V/V)
  6. additionThe fractions containing the desired compound
  7. customwere collected
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-fa055fb3650840f7a2a294a62f64e046
Source dataset
uspto-grants-1993_04
Patent number
US05202437

Reaction notes

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