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

HRID 1091006

反応式

HRID 1091006 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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%):

後処理

  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)

出典と根拠

ORDレコード
ord-5a87615f9b224512aed0b446523c265a
出典データセット
uspto-grants-1992_01
特許番号
US05084447

関連ノート

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