Ethyl Acetate → HCID 178511758, 화합물

HRID 1707443노트

반응식

HRID 1707443 반응식
Cl.[C:2]1([CH:8]([O:15][C:16]([C:18]2[N:23]3[C:24](=[O:27])[C@@H:25]([NH2:26])[C@H:22]3[S:21][CH2:20][C:19]=2[CH2:28][S:29][C:30]2[N:31]=[N:32][NH:33][CH:34]=2)=[S:17])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>ClCCl>[C:2]1([CH:8]([O:15][C:16]([C:18]2[N:23]3[C:24](=[O:27])[C@@H:25]([NH2:26])[C@H:22]3[S:21][CH2:20][C:19]=2[CH2:28][S:29][C:30]2[N:31]=[N:32][NH:33][CH:34]=2)=[S:17])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 178479291HCID 178479291, 화합물

생성물 1

HCID 178511758HCID 178511758, 화합물수율 10%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 7β-phenylacetamido-3-(1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (629 mg: 1 mMol.) in dichloromethane (7 ml) under ice cooling are added pyridine (162 μl: 2 mMol.) and phosphorus pentachloride (380 mg: 1.8 mMol.), and the mixture is stirred at room temperature for 40 minutes. The solution is dropwise added into a solution of 1,3-butanediol (0.46 ml) in dichloromethane (2 ml) at -30° C. After stirring under ice cooling for 30 minutes, the reaction mixture is diluted with water and extracted with dichloromethane. The extract is dried over sodium sulfate and concentrated under reduced pressure. The residue gives powder (518 mg) containing 7β-amino-3-(1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester hydrochloride from ethyl acetate--dichloromethane. This powder (100 mg) is suspended in dichloromethane, shaken with 5% aqueous sodium hydrogen carbonate, dried over sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel chromatography to give 7β-amino-3-(1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (10 mg). Yield: 10%.

후처리

  1. dry with materialdried over sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-bce0447bc16f42218e32bb99dbc3e467
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05352792

반응 노트

불러오는 중…