Acetic Acid → HCID 15056146, compound

HRID 1650843Notes

Reaction equation

HRID 1650843 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([CH2:23][N:24]2[CH2:28][CH2:27][N:26]([CH3:29])[C:25]2=[O:30])[CH2:6]1)(=O)C.C[O-].[Na+].C(O)(=O)C>CO.C(OCC)(=O)C.O1CCCC1>[SH:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([CH2:23][N:24]2[CH2:28][CH2:27][N:26]([CH3:29])[C:25]2=[O:30])[CH2:6]1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 15056145(2S,4S)-4-acetylthio-2-(3-methyl-2-oxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)-pyrrolidine

Product 1

HCID 15056146HCID 15056146, compoundYield 79.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4S)-4-acetylthio-2-(3-methyl-2-oxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.72 g) in methanol (40 ml) was added 28% sodium methoxide in methanol solution (0.83 ml) and the mixture was stirred under ice-cooling for 30 minutes. Acetic acid (0.25 ml) was added to the reaction mixture at the same temperature. The mixture was evaporated in vacuo to give a residue. The residue was dissolved in a mixture of ethyl acetate (80 ml) and tetrahydrofuran (30 ml) and the solution was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (100 g) eluting with a mixture of chloroform and methanol (19:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-4-mercapto-2-(3-methyl-2-oxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.23 g).

Workup

  1. temperaturecooling for 30 minutes
  2. customThe mixture was evaporated in vacuo
  3. customto give a residue
  4. washthe solution was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe resulting residue was chromatographed on silica gel (100 g)
  8. washeluting with a mixture of chloroform and methanol (19:1, V/V)
  9. additionThe fractions containing the desired compound
  10. customwere collected
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-0f20903810924b26a44f1c67a429d4e8
Source dataset
uspto-grants-1990_05
Patent number
US04925838

Reaction notes

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