Ammonium Chloride → (2S,4S)-2-azidomethyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine

HRID 1590491Notes

Reaction equation

HRID 1590491 reaction equation
CS(O[CH2:6][C@@H:7]1[CH2:11][C@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][N:8]1[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:33])(=O)=O.[N-:45]=[N+:46]=[N-:47].[Na+].[Cl-].[NH4+]>CN(C)C=O>[N:45]([CH2:6][C@@H:7]1[CH2:11][C@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:9][N:8]1[C:32]([O:34][CH2:35][C:36]1[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=1)=[O:33])=[N+:46]=[N-:47]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 15056119(2S,4S)-2-mesyloxymethyl-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

Product 1

HCID 57090966(2S,4S)-2-azidomethyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidineYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S,4S)-2-(methanesulfonyloxy)methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (7.1 g) in dimethylformamide (70 ml) was added sodium azide (1.09 g) and ammonium chloride (0.90 g) and the mixture was stirred at 80°-90° C. for 3 hours. The reaction mixture was poured into ice-water (200 ml) and extracted twice with ethyl acetate (200 ml). The extract was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (200 g) eluting with n-hexane and ethyl acetate (2:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-2-azidomethyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (5.20 g).

Workup

  1. extractionextracted twice with ethyl acetate (200 ml)
  2. washThe extract was washed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe resulting residue was chromatographed on silica gel (200 g)
  6. washeluting with n-hexane and ethyl acetate (2:1, V/V)
  7. additionThe fractions containing the desired compound
  8. customwere collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-e3b729ca7d5f48968b6e15125e3b971b
Source dataset
uspto-grants-1993_04
Patent number
US05202437

Reaction notes

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