Dichloromethane → (1R,2R,4S)-2-{[(Benzyloxycarbonyl) sulfamoyl]amino}-4-(dimethylcarbamoyl)cyclohexyl methanesulfonate

HRID 64045Notes

Reaction equation

[CH3:1][N:2]([CH3:27])[C:3]([C@@H:5]1[CH2:10][C@@H:9]([NH:11][S:12]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:14])=[O:13])[C@H:8]([OH:26])[CH2:7][CH2:6]1)=[O:4].C(Cl)Cl.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(N(CC)CC)C>[CH3:31][S:32]([O:26][C@@H:8]1[CH2:7][CH2:6][C@H:5]([C:3](=[O:4])[N:2]([CH3:27])[CH3:1])[CH2:10][C@H:9]1[NH:11][S:12](=[O:13])(=[O:14])[NH:15][C:16]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:25])(=[O:34])=[O:33]

Participants

Conditions

Temperature: 0 °C

Procedure

Benzyl {[(1R,2R,5S)-5-(dimethylcarbamoyl)-2-hydroxycyclohexyl]sulfamoyl}carbamate (1.00 g) was added to methylene chloride (10 ml), and the obtained solution was then cooled to approximately 0° C. Triethylamine (0.52 ml) was added to the reaction solution, and methanesulfonyl chloride (0.28 ml) was then added dropwise to the mixed solution. The obtained mixture was stirred for approximately 1 hour. The precipitated crystals were collected by filtration, and were then washed with methylene chloride (1 ml). The obtained crystals were dried under reduced pressure to obtain 866 mg of the title compound (yield: 72%).

Workup

additionwas then added dropwise to the mixed solution
filtrationThe precipitated crystals were collected by filtration
washwere then washed with methylene chloride (1 ml)
customThe obtained crystals were dried under reduced pressure

Sources & evidence

ORD record: ord-25067822fe3f4882b79d0365559895f8
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447118B2

Reaction notes

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