Pyridine → HCID 178477371, 화합물

HRID 979687

반응식

HRID 979687 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[N:14]=[C:15]([NH:18][C:19](=[O:22])[CH2:20][Cl:21])[S:16][CH:17]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.[C:29]1([CH:35]([O:42][C:43]([C:45]2[N:50]3[C:51](=[O:54])[C@@H:52]([NH2:53])[C@H:49]3[S:48][CH2:47][C:46]=2[CH:55]([S:57][C:58]2[NH:62][N:61]=[N:60][N:59]=2)[CH3:56])=[O:44])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.N1C=CC=CC=1>C(Cl)Cl>[C:29]1([CH:35]([O:42][C:43]([C:45]2[N:50]3[C:51](=[O:54])[C@@H:52]([NH:53][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:13]4[N:14]=[C:15]([NH:18][C:19](=[O:22])[CH2:20][Cl:21])[S:16][CH:17]=4)[C@H:49]3[S:48][CH2:47][C:46]=2[CH:55]([S:57][C:58]2[NH:62][N:61]=[N:60][N:59]=2)[CH3:56])=[O:44])[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 12763201alpha-t-Butyloxycarbonylamino-alpha-[2-(chloroacetamido)thiazol-4-yl)acetic acidHCID 178477368HCID 178477368, 화합물

생성물 1

HCID 178477371HCID 178477371, 화합물수율 62.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of 349 mg of α-t-butyloxycarbonylamino-α-[2-(chloroacetamido)thiazol-4-yl]acetic acid in 5 ml of methylene chloride is added 249 mg of phosphorous pentachloride, and the mixture is stirred at room temperature. The mixture is added dropwise under stirring to the solution of 494 mg of 7β-amino-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid diphenylmethyl ester dissolved in 5 ml of methylene chloride, followed by the addition of 474 mg of pyridine. After that, the stirring is continued for further 1 hour at room temperature. The reaction solution is washed with 0.5N hydrochloric acid and then with water, and dried. The oily product obtained by the distillation of the solvent is purified by a column chromatography packed with silica gel. The procedure gives 513 mg of 7β-{α-t-butyloxycarbonylamino-α-[2-(chloroacetamido)thiazol-4-yl]acetamido}-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid diphenylmethyl ester.

후처리

  1. additionThe mixture is added dropwise
  2. washThe reaction solution is washed with 0.5N hydrochloric acid
  3. dry with materialwith water, and dried
  4. customThe oily product obtained by the distillation of the solvent
  5. customis purified by a column chromatography

출처 및 근거

ORD 기록
ord-0f9af74313af4b7b862ae9bc92d45f7d
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04668783

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