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

HRID 1091008

반응식

HRID 1091008 반응식
[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

참가 물질

5

반응물 2

HCID 7623Tributyl phosphiteHCID 540211893-Bromo-7-[(phenoxyacetyl)amino]-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (diphenylmethyl)ester

생성물 1

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

시약·촉매·용매 2

HCID 24385Nickel Dichloride촉매2회HCID 1140Toluene용매

실험 절차

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%):

후처리

  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)

출처 및 근거

ORD 기록
ord-d19399c0952d478e8702ac24718e13f3
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05084447

연결된 노트

불러오는 중…