Potassium ethanethioate → HCID 57262936, compound

HRID 1034504Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@H:14](OS(C)(=O)=O)[CH2:13][C@H:12]2[CH2:21][NH:22][S:23](=[O:26])(=[O:25])[NH2:24])=[O:10])=[CH:5][CH:4]=1.[C:29]([O-:32])(=[S:31])[CH3:30].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@@H:14]([S:31][C:29](=[O:32])[CH3:30])[CH2:13][C@H:12]2[CH2:21][NH:22][S:23](=[O:25])(=[O:26])[NH2:24])=[O:10])=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of crude (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-methanesulfonyloxy-2-sulfamoylaminomethylpyrrolidine (2.26 g) obtained in Step 5 in dimethylformamide (12 ml), potassium thioacetate (1.7 g) is added. The mixture is stirred at 60° C. for 5 hours. The reaction mixture is diluted with ethyl acetate, successively washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography (toluene:ethyl acetate=1:2) to give (2S,4S)-1-p-methoxybenzyloxycarbonyl-4-acetylthio-2-sulfamoylaminomethylpyrrolidine (971 mg). NMR δ(CDCl3) ppm: 1.8(br s, 1H), 2.33(s, 3H), 2.4 to 2.7(m, 1H), 3.1 to 3.5(m), 3.81(s, 3H), 3.9 to 4.2(m, 2H), 5.05(s, 2H), 6.89(d, J=8.8 Hz, 2H), 7.30(d, J=8.8 Hz, 2H). IR ν (CHCl3) cm-1 : 3414, 3276, 1688.

Workup

washsuccessively washed with water and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue is purified by silica gel column chromatography (toluene:ethyl acetate=1:2)

Sources & evidence

ORD record: ord-86e677cb0c324b05bda361f93d7b6b85
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05317016

Reaction notes

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