Acetic Acid → (2S,4S)-4-mercapto-1-methyl-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine

HRID 1590507Notes

Reaction equation

HRID 1590507 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8]([CH3:10])[C@H:7]([CH2:11][N:12]2[CH2:16][CH2:15][NH:14][C:13]2=[O:17])[CH2:6]1)(=O)C.C[O-].[Na+].C(O)(=O)C>CO>[SH:4][C@@H:5]1[CH2:9][N:8]([CH3:10])[C@H:7]([CH2:11][N:12]2[CH2:16][CH2:15][NH:14][C:13]2=[O:17])[CH2:6]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 18639285(2S,4S)-4-acetylthio-1-methyl-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine

Product 1

HCID 18639286(2S,4S)-4-mercapto-1-methyl-2-(2-oxoimidazolidin-1-yl)methylpyrrolidineYield 39.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (2S,4S)-4-acetylthio-1-methyl-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine (1.83 g) in methanol (20 ml) was added 28% sodium methoxide in methanol solution (1.50 ml) at -10°~-5° C. and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added acetic acid (0.45 ml) at the same temperature and the mixture was evaporated in vacuo. The resulting residue was chromatographed on silica gel (100 g) eluting with a mixture of chloroform and methanol (9:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-4-mercapto-1-methyl-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine (0.60 g).

Workup

  1. customthe mixture was evaporated in vacuo
  2. customThe resulting residue was chromatographed on silica gel (100 g)
  3. washeluting with a mixture of chloroform and methanol (9:1 V/V)
  4. additionThe fractions containing the desired compound
  5. customwere collected
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e468cb0bfb0e4d51b1c6e1c67d351949
Source dataset
uspto-grants-1993_04
Patent number
US05202437

Reaction notes

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