Iodoacetamide → (2S,4R)-4-t-butyldimethylsilyloxy-2-(carbamoylmethyl)thiomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 1088950Notes

Reaction equation

HRID 1088950 reaction equation
C([S:4][CH2:5][C@@H:6]1[CH2:10][C@@H:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:8][N:7]1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20])(=O)C.C[O-].[Na+].CO.I[CH2:38][C:39]([NH2:41])=[O:40]>CO>[Si:12]([O:11][C@H:9]1[CH2:8][N:7]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[C@H:6]([CH2:5][S:4][CH2:38][C:39](=[O:40])[NH2:41])[CH2:10]1)([C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 23694274Sodium methanolate methanolHCID 56989934(2S,4R)-2-acetylthiomethyl-4-t-butyldimethylsilyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 57024589(2S,4R)-4-t-butyldimethylsilyloxy-2-(carbamoylmethyl)thiomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 102.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S,4R)-2-acetylthiomethyl-4-t-butyldimethylsilyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.0 g) in methanol (20 ml) was added 28% sodium methoxide-methanol solution (0.98 ml) under an atmosphere of nitrogen at 0° C. After stirring at the same temperature for 10 minutes, to this reaction mixture was added 2-iodoacetamide (1.02 g) under the same condition. The mixture was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (100 ml). The solution was washed with saturated aqueous sodium hydrogen carbonate and saturated sodium chloride successively, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give (2S,4R)-4-t-butyldimethylsilyloxy-2-(carbamoylmethyl)thiomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.11 g).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in ethyl acetate (100 ml)
  4. washThe solution was washed with saturated aqueous sodium hydrogen carbonate and saturated sodium chloride successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-eb28d889b2f44323a477a3cadc35bf9a
Source dataset
uspto-grants-1990_10
Patent number
US04963543

Reaction notes

Loading…