Pyridine → 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-[5-(tetrazol-1-yl)-pentanoylthio]-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester

HRID 414751노트

반응식

HRID 414751 반응식
[CH2:1]([O:4][C:5](=[O:41])[C:6]([N:26]1[C@H:29]([SH:30])[C@@H:28]([C@H:31]([O:33][C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])[CH3:32])[C:27]1=[O:40])=[P:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH2:3].N1C=CC=CC=1.[N:48]1([CH2:53][CH2:54][CH2:55][CH2:56][C:57](Cl)=[O:58])[CH:52]=[N:51][N:50]=[N:49]1>C(Cl)Cl.CN(C)C1C=CN=CC=1.[Ag]>[CH2:1]([O:4][C:5](=[O:41])[C:6]([N:26]1[C@H:29]([S:30][C:57](=[O:58])[CH2:56][CH2:55][CH2:54][CH2:53][N:48]2[CH:52]=[N:51][N:50]=[N:49]2)[C@@H:28]([C@H:31]([O:33][C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])[CH3:32])[C:27]1=[O:40])=[P:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH2:3]

참가 물질

7

반응물 3

HCID 1049PyridineHCID 140845622-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl esterHCID 178034065-(Tetrazol-1-yl)-valeric acid chloride

생성물 1

HCID 571673172-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-[5-(tetrazol-1-yl)-pentanoylthio]-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 23954Silver촉매HCID 6344Dichloromethane용매2회

실험 절차

1.74 g of the silver salt of 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester are dissolved in 30 ml of methylene chloride, and, at 0°, 0.41 ml of pyridine, 50 mg of 4-dimethylaminopyridine and then, dropwise, a solution of 0.87 g of 5-(tetrazol-1-yl)-valeric acid chloride in 15 ml of methylene chloride are added. After stirring for 30 minutes at 0°, the solid material is filtered off over Hyflo and the filtrate is washed with aqueous sodium bicarbonate solution and then with brine. After drying over MgSO4, the solution is concentrated by evaporation. The residue is purified by chromatography over silica gel (eluant toluene/ethyl acetate: 9:1 to 1:1). TLC (ethyl acetate) Rf =0.33; IR (CH2Cl2): 1750, 1690, 1620 cm-1.

후처리

  1. filtrationthe solid material is filtered off over Hyflo
  2. washthe filtrate is washed with aqueous sodium bicarbonate solution
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe solution is concentrated by evaporation
  5. customThe residue is purified by chromatography over silica gel (eluant toluene/ethyl acetate: 9:1 to 1:1)

출처 및 근거

ORD 기록
ord-944b9315c8d148288c1200bf6f440897
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04794109

반응 노트

불러오는 중…