Dimethyl Sulfoxide → (2S,4S)-N-(p-nitrobenzyloxycarbonyl)-4-tritylthioprolinal

HRID 725942Notes

Reaction equation

HRID 725942 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][C@@H:13]1[CH2:17][C@H:16]([S:18][C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([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)[CH2:15][N:14]1[C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=1)=[O:39].C(N(CC)CC)C.[Cl-].[NH4+]>C(Cl)Cl>[N+:48]([C:45]1[CH:44]=[CH:43][C:42]([CH2:41][O:40][C:38]([N:14]2[CH2:15][C@@H:16]([S:18][C:19]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:17][C@H:13]2[CH:12]=[O:11])=[O:39])=[CH:47][CH:46]=1)([O-:50])=[O:49]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 15056118(2S,4S)-2-hydroxymethyl-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

Product 1

HCID 57143552(2S,4S)-N-(p-nitrobenzyloxycarbonyl)-4-tritylthioprolinal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethyl sulfoxide (1.06 ml, 14.9 mmol) was added to a solution of oxalyl chloride (0.648 ml, 7.43 mmol) in methylene chloride (40 ml) at -78° C. in a nitrogen stream over 2 minutes. The resulting reaction solution was stirred at the same temperature for 10 minutes. To this reaction solution, a solution of (2S,4S)-2-hydroxymethyl-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine (2.47 g, 4.45 mmol) in methylene chloride (10 ml) was added dropwise over 5 minutes. This reaction mixed solution was stirred for 10 minutes and then triethylamine (3.11 ml, 22.3 mmol) was added dropwise over 2 minutes. This reaction solution was reverted to room temperature over 30 minutes, brought together with saturated aqueous ammonium chloride to terminate the reaction, and extracted with ethyl acetate. The organic layer was washed successively with water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off in vacuo to give a crude product of (2S,4S)-N-(p-nitrobenzyloxycarbonyl)-4-tritylthioprolinal.

Workup

  1. customThe resulting reaction solution
  2. additionThis reaction mixed solution
  3. stirringwas stirred for 10 minutes
  4. waitThis reaction solution was reverted to room temperature over 30 minutes
  5. customto terminate
  6. customthe reaction
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed successively with water and saturated aqueous sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-86a248f48a694ab5b22aa76bffc7c098
Source dataset
uspto-grants-1998_01
Patent number
US05707987

Reaction notes

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