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

HRID 1091008

反応式

HRID 1091008 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:49]CCCC)([O:44][CH2:45][CH2:46][CH2:47][CH3:48])[O:39][CH2:40][CH2:41][CH2:42][CH3:43]>C1(C)C=CC=CC=1.[Ni](Cl)Cl>[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:39][CH2:40][CH2:41][CH2:42][CH3:43])([O:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:49])[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

5

反応物 2

HCID 7623Tributyl 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 544356247-[(Phenoxyacetyl)amino]-8-oxo-3-(dibutoxyphosphinyl)-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid (diphenylmethyl)ester収率 24%

試薬・触媒・溶媒 2

HCID 24385Nickel Dichloride触媒2 回HCID 1140Toluene溶媒

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 (2 g, 3.6 mmol) in toluene (50 mL) was added tri-n-butyl phosphite (15 mL) and nickel(II)chloride (50 mg, 039 mmol). The reaction was brought to reflux under nitrogen. Each hour, the reaction was cooled and an additional portion of nickel(II)chloride (50 mg, 0.39 mmol) was added. This process was continued for a total of six hours. The reaction was concentrated in vacuo and the residue purified by flash chromatography on silica gel (25%-50% ethyl acetate/hexanes) to provide 7-[(Phenoxyacetyl)amino]-8-oxo-3-(dibutoxyphosphinyl)-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid (diphenylmethyl)ester (588 mg, 24%):

後処理

  1. temperatureto reflux under nitrogen
  2. temperatureEach hour, the reaction was cooled
  3. customwas continued for a total of six hours
  4. concentrationThe reaction was concentrated in vacuo
  5. customthe residue purified by flash chromatography on silica gel (25%-50% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-d19399c0952d478e8702ac24718e13f3
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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