Dimethylformamide → HCID 131714267, compound

HRID 867634Notes

Reaction equation

[CH3:1][O-:2].[Li+].Cl[N:5]([CH:15]1[CH2:18][N:17]([S:19]([OH:22])(=[O:21])=[O:20])[C:16]1=[O:23])[C:6](=[O:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[K].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:33][N:34]([CH3:37])[CH:35]=O>CO>[CH2:33]([N+:34]([CH2:37][CH2:16][CH2:15][CH3:18])([CH2:8][CH2:13][CH2:12][CH3:11])[CH2:35][CH2:9][CH2:10][CH3:11])[CH2:6][CH2:7][CH3:8].[CH3:1][O:2][C:15]1([NH:5][C:6](=[O:14])[CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:18][N:17]([S:19]([OH:22])(=[O:20])=[O:21])[C:16]1=[O:23]

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirring solution of lithium methoxide (160 mg) in 5 ml of methanol cooled to -78° C. is added a solution of N-chloro-N-(2-oxo-1-sulfo-3-azetidinyl)-2-phenylacetamide, potassium salt (149 mg) in 10 ml of dry dimethylformamide. After addition is complete, the mixture is stirred for 15 minutes at -78° C., poured into 0.5N monobasic potassium phosphate solution (100 ml), and washed three times with methylene chloride. Tetrabutylammonium bisulfate (213 mg) is added to the aqueous layer, which is then extracted three times with methylene chloride. The combined extracts are dried (sodium sulfate), and solvent is removed in vacuo giving an oil (271 mg). Chromatography of the oil on silica gel (25 g) and elution with 4% methanol:96% methylene chloride yields 149 mg of the product as an oil.

Workup

additionAfter addition
washwashed three times with methylene chloride
additionTetrabutylammonium bisulfate (213 mg) is added to the aqueous layer, which
extractionis then extracted three times with methylene chloride
dry with materialThe combined extracts are dried (sodium sulfate), and solvent
customis removed in vacuo

Sources & evidence

ORD record: ord-0574c7df08df499fbd3198023934448f
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04775670

Reaction notes

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