Sodium Sulfite → HCID 10870082, compound

HRID 580066Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:15]([CH2:16][OH:17])[NH:14][C:13]1=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClS([N:23]=[C:24]=[O:25])(=O)=O.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:15]([CH2:16][O:17][C:24](=[O:25])[NH2:23])[NH:14][C:13]1=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -15 °C

Procedure

In 16 ml of dry dichloromethane is dissolved 0.50 g of (3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-azetidinone obtained in Example 37 and, on cooling at -15° C., 0.368 g of chlorosulfonyl isocyanate is added, followed by stirring for 30 minutes. A 15-ml aqueous solution of 0.72 g of sodium sulfite is added and the solution is warmed to room temperature, followed by stirring for 1 hour. The dichloromethane is distilled off under reduced pressure and the residue is extracted twice with ethyl acetate-tetrahydrofuran (3:1, v/v). The extract is washed with aqueous sodium chloride, dried over mangesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography [eluent: chloroform-ethyl acetate-methanol (40:55:5, v/v/v)] to give 0.323 g of (3S,4S)-3-benzyloxycarbonylamino-4-carbamoyloxymethyl-2-azetidinone.

Workup

temperaturethe solution is warmed to room temperature
stirringby stirring for 1 hour
distillationThe dichloromethane is distilled off under reduced pressure
extractionthe residue is extracted twice with ethyl acetate-tetrahydrofuran (3:1
washThe extract is washed with aqueous sodium chloride
dry with materialdried over mangesium sulfate
concentrationconcentrated under reduced pressure
customThe residue is purified by silica gel column chromatography [eluent

Sources & evidence

ORD record: ord-1506d1bf0e9d458288087bbb4297fe9c
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04751299

Reaction notes

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