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

HRID 1091007

反応式

HRID 1091007 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:43]C)([O:41][CH3:42])[O:39][CH3:40]>>[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:41][CH3:42])([O:39][CH3:40])=[O:43])[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 8472Trimethyl 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 541540907-[(Phenoxyacetyl)amino]-8-oxo-3-(dimethoxyphosphinyl)-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (diphenylmethyl)ester収率 25%

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 (1.12 g, 2 mmol) in trimethyl phosphite (5 mL) was refluxed under nitrogen for two hours. After cooling, the reaction was poured into hexanes. The supernatant was removed and the residue purified by flash chromatography on silica gel (50% ethyl acetate/hexanes to 100% ethyl acetate) to provide 7-[(phenoxyacetyl)amino]-8-oxo-3-(dimethoxyphosphinyl)-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (diphenylmethyl)ester (300 mg; 25%):

後処理

  1. temperatureAfter cooling
  2. customThe supernatant was removed
  3. customthe residue purified 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-bb87ddb5c08043b2a407170212642af2
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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