Acetic Acid → HCID 57027456, compound

HRID 1586747Notes

Reaction equation

HRID 1586747 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[CH2:29][CH2:28][CH2:27][N:26]3[N:30]=[CH:31][CH:32]=[C:25]23)[CH2:6]1)(=O)C.C[O-].[Na+].C(O)(=O)C>CO.O1CCCC1>[SH:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)=[O:11])[C@H:7]([CH2:23][N:24]2[CH2:29][CH2:28][CH2:27][N:26]3[N:30]=[CH:31][CH:32]=[C:25]23)[CH2:6]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 57260090HCID 57260090, compound

Product 1

HCID 57027456HCID 57027456, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl) -2-{4,5,6,7-tetrahydropyrazolo [1,5-a]pyrimidin-4-yl}methylpyrrolidine (2.22 g) in a mixture of methanol (40 ml) and tetrahydrofuran (20 ml) was added 28% sodium methoxide in methanol solution (0.98 ml) under ice-cooling and the mixture was stirred at the same temperature for 15 minutes. To the reaction mixture was added acetic acid (0.29 ml) at the same temperature and the mixture was evaporated in vacuo. The resulting residue was dissolved in a mixture of ethyl acetate (100 ml) and water (30 ml). The organic layer was separated and washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting residue was chromatographed on silica gel (150 g) eluting with a mixture of chloroform and methanol (19:1, V/V). The fractions containing the desired compound were collected and concentrated in vacuo to give (2S,4S)-4-mercapto-1-(4-nitrobenzyloxycarbonyl) -2-{4,5,6,7-tetrahydropyrazolo[ 1,5-a]pyrimidin-4-yl}methylpyrrolidine (1.80 g).

Workup

  1. temperaturecooling
  2. customthe mixture was evaporated in vacuo
  3. dissolutionThe resulting residue was dissolved in a mixture of ethyl acetate (100 ml) and water (30 ml)
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was chromatographed on silica gel (150 g)
  9. washeluting with a mixture of chloroform and methanol (19:1, V/V)
  10. additionThe fractions containing the desired compound
  11. customwere collected
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdf816c22d484904945728616a7ff431
Source dataset
uspto-grants-1993_06
Patent number
US05215983

Reaction notes

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