Thioacetic acid → HCID 15086222, compound

HRID 1613995Notes

Reaction equation

HRID 1613995 reaction equation
[OH-].[Ca+2].[OH-].[CH2:4]([O:7][C:8]([N:10]1[CH2:14][C@H:13](OS(C)(=O)=O)[CH2:12][C@H:11]1[CH2:20][N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)=[O:9])[CH:5]=[CH2:6].[C:26]([SH:29])(=[O:28])[CH3:27]>CC(C)CC(=O)C>[C:26]([S:29][C@@H:13]1[CH2:14][N:10]([C:8]([O:7][CH2:4][CH:5]=[CH2:6])=[O:9])[C@H:11]([CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)[CH2:12]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 10484Thioacetic acidHCID 6093208Calcium HydroxideHCID 15086221HCID 15086221, compound

Product 1

HCID 15086222HCID 15086222, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
82.5 °C

Procedure

To a solution of calcium hydroxide (2.25 g) and (2S,4R)-1-allyloxycarbonyl-2-(imidazol-1-yl)methyl-4-methanesulfonyloxypyrrolidine (10 g) in 4-methyl-2-pentanone (60 ml) was added dropwise thioacetic S-acid (4.38 ml) with stirring below 45° C. The solvent (18 ml) of the mixture was removed under reduced pressure at 40-45° C. The resulting suspension was heated at 80-85° C. for 2 hours. After cooling, water (20 ml) and ethyl acetate (20 ml) was added to the reaction mixture. The insoluble material was filtered off and washed with ethyl acetate (30 ml). The filtrate and washing were combined. The organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo to give (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(imidazol-1-yl)methylpyrrolidine (7.94 g).

Workup

  1. customThe solvent (18 ml) of the mixture was removed under reduced pressure at 40-45° C
  2. temperatureAfter cooling
  3. additionwater (20 ml) and ethyl acetate (20 ml) was added to the reaction mixture
  4. filtrationThe insoluble material was filtered off
  5. washwashed with ethyl acetate (30 ml)
  6. washThe filtrate and washing
  7. washThe organic layer was washed with saturated aqueous sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-f0a48d4f7a8145e58db92cb1da62eb2c
Source dataset
uspto-grants-1993_03
Patent number
US05194624

Reaction notes

Loading…