Dichloromethane → HCID 21310371, compound

HRID 582480Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[OH:12][CH2:13][C@@H:14]1[O:20][C@@H:19]2[N:16]([C:17](=[O:21])[CH2:18]2)[CH2:15]1.C(N(CC)CC)C.[Cl:29]CCl>>[Cl:29][C:6]1[CH:5]=[CH:4][C:3]([S:8]([O:12][CH2:13][C@@H:14]2[O:20][C@@H:19]3[N:16]([C:17](=[O:21])[CH2:18]3)[CH2:15]2)(=[O:10])=[O:9])=[CH:2][CH:7]=1

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 8471Triethylamine

HCID 761872-Chlorobenzenesulfonyl chloride

HCID 30502592-Hydroxymethylclavam2×

Product 1

HCID 21310371HCID 21310371, compoundYield 76%

Procedure

Chlorobenzenesulfonyl chloride (478 mg, 2.27 mmol) was added to an ice-cooled solution of (3R,5S)-3-hydroxymethyl-4-oxa-1-azabicyclo[3,2,0]heptan-7-one (ref. compound 2) (250 mg, 1.75 mmol) and triethylamine (230 mg, 2.27 mmol) in dichloromethane (5 ml). The mixture was stirred at room temperature over night. After removal of solvent, the residue was purified by silica gel column chromatography using chloroform-ethyl acetate (5:1) as eluent and 420 mg of (3R,5S)-3-(4-chlorobenzenesulfonyl)oxymethyl-4-oxa-1-azabicyclo[3,2,0] heptan-7-one was obtained as white solid.

Workup

customAfter removal of solvent
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-a5240291c5bd4542bbde026601667120
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05925633

Reaction notes

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