Triethyl phosphite → 7-[(Phenoxyacetyl)amino]-8-oxo-3-(diethoxyphosphinyl)-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (diphenylmethyl)ester

HRID 1091006

Reaktionsgleichung

Reaktionsgleichung von HRID 1091006
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:18]3[CH:21]([CH2:22][CH2:23][C:24]=2Br)[CH:20]([NH:26][C:27](=[O:36])[CH2:28][O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:19]3=[O:37])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[P:38]([O:45]CC)([O:42][CH2:43][CH3:44])[O:39][CH2:40][CH3:41]>>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:18]3[CH:21]([CH2:22][CH2:23][C:24]=2[P:38]([O:42][CH2:43][CH3:44])([O:39][CH2:40][CH3:41])=[O:45])[CH:20]([NH:26][C:27](=[O:36])[CH2:28][O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:19]3=[O:37])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

3

Edukt 2

HCID 31215Triethyl phosphiteHCID 540211893-Bromo-7-[(phenoxyacetyl)amino]-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (diphenylmethyl)ester

Produkt 1

HCID 544202427-[(Phenoxyacetyl)amino]-8-oxo-3-(diethoxyphosphinyl)-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (diphenylmethyl)esterAusbeute 16 %

Versuchsvorschrift

A solution of 3-bromo-7-[(phenoxyacetyl)amino]-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (diphenylmethyl)ester (784 mg, 1.4 mmol) in triethyl phosphite (4 mL) was refluxed under nitrogen for 90 minutes. After cooling, the reaction was poured into hexanes. The supernatant liquid was decanted from the resulting semi-solid which was then dissolved in ethyl acetate and purified by flash-chromatography on silica gel (50% ethyl acetate/hexanes to 100% ethyl acetate) to provide 7-[(phenoxyacetyl)amino]-8-oxo-3-(diethoxyphosphinyl)-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (diphenylmethyl) ester (100 mg; 16%):

Aufarbeitung

  1. temperatureAfter cooling
  2. customThe supernatant liquid was decanted from the resulting semi-solid which
  3. dissolutionwas then dissolved in ethyl acetate
  4. custompurified by flash-chromatography on silica gel (50% ethyl acetate/hexanes to 100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-5a87615f9b224512aed0b446523c265a
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05084447

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