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Trifluoroacetic acid → 7beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid

HRID 1609667
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HRID 1609667 반응식
FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.[NH2:16][C:17]1[S:21][N:20]=[C:19]([C:22](=[N:53][O:54][CH2:55][C:56]([OH:58])=[O:57])[C:23]([NH:25][C@@H:26]2[C:51](=[O:52])[N:28]3[C:29]([C:35]([O:37]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:36])=[C:30]([CH2:33][Cl:34])[CH2:31][S:32][C@H:27]23)=[O:24])[N:18]=1.C(OC(C)C)(C)C>C(Cl)Cl.CCCCCC>[NH2:16][C:17]1[S:21][N:20]=[C:19]([C:22](=[N:53][O:54][CH2:55][C:56]([OH:58])=[O:57])[C:23]([NH:25][C@@H:26]2[C:51](=[O:52])[N:28]3[C:29]([C:35]([OH:37])=[O:36])=[C:30]([CH2:33][Cl:34])[CH2:31][S:32][C@H:27]23)=[O:24])[N:18]=1
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참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131718944Benzhydryl 7beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

생성물 1

HCID 1317189457beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid
수율 106%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

To a solution of trifluoroacetic acid (20 ml) and anisole (10 ml) in methylene chloride (50 ml) was added benzhydryl 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl) -2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (7.0 g) at 0°~5° C. under stirring. The stirring was continued for 2 hours at the same temperature. The reaction mixture was poured into a cold mixture of diisopropyl ether (400 ml) and n-hexane (200 ml). The resulting precipitates were collected by filtration to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid (syn isomer) (5.5 g).

후처리

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration

출처 및 근거

ORD 기록
ord-4884ab657e2a474eb78b7a955b4026e9
출처 데이터셋
uspto-grants-1995_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05401734

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