Thioacetic acid → HCID 15086180, compound

HRID 1088635Notes

Reaction equation

HRID 1088635 reaction equation
[N:1]1([CH2:6][C@@H:7]2[CH2:11][C@@H:10](OS(C)(=O)=O)[CH2:9][N:8]2[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[CH:5]=[CH:4][N:3]=[CH:2]1.[C:30]([SH:33])(=[O:32])[CH3:31].[H-].[Na+]>CN(C)C=O>[C:30]([S:33][C@@H:10]1[CH2:9][N:8]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[C@H:7]([CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH2:11]1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 10484Thioacetic acidHCID 24758Sodium hydrideHCID 15086213HCID 15086213, compound

Product 1

HCID 15086180HCID 15086180, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (2S,4R)-2-(imidazol-1-yl)methyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.76 g) in dimethylformamide (2 ml) was added to a mixture of thioacetic S-acid (0.16 ml) and sodium hydride (62.8 % in oil suspension, 0.08 g) in dimethylformamide (5 ml) under nitrogen stream and the mixture was heated at 70°-75° C. for 5 hours. The mixture was poured into ice-water (70 ml), extracted with ethyl acetate (70 ml), dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (20 g) and eluted with a mixture of methanol and chloroform (2:98, V/V) to give (2S,4S)-4-acetylthio-2-(imidazol-1-yl)methyl-1-(-4-nitrobenzyloxycarbonyl)pyrrolidine (0.38 g).

Workup

  1. temperaturethe mixture was heated at 70°-75° C. for 5 hours
  2. extractionextracted with ethyl acetate (70 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a syrup
  6. washeluted with a mixture of methanol and chloroform (2:98, V/V)

Sources & evidence

ORD record
ord-7f1056dcfc434e8a8d4d7fe785cfa1c2
Source dataset
uspto-grants-1990_10
Patent number
US04963544

Reaction notes

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