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Hydrochloric Acid → Benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

HRID 1247920
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HRID 1247920 반응식
Cl.[NH2:2][CH:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:7]([CH2:10][Cl:11])[CH2:8][S:9][C@H:4]12.CN(C)C1C=CC=CC=1.Cl.[CH2:40]([O:42][N:43]=[C:44]([C:48]1[N:52]=[C:51]([NH2:53])[S:50][N:49]=1)[C:45](Cl)=[O:46])[CH3:41].Cl>C(Cl)Cl.O>[CH2:40]([O:42][N:43]=[C:44]([C:48]1[N:52]=[C:51]([NH2:53])[S:50][N:49]=1)[C:45]([NH:2][CH:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14][CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:13])=[C:7]([CH2:10][Cl:11])[CH2:8][S:9][C@H:4]12)=[O:46])[CH3:41]
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 13239629Benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochlorideHCID 867392542-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochloride

생성물 1

HCID 131714229Benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate
수율 88.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

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온도
5 °C

실험 절차

To a suspension of diphenylmethyl 7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride (27 g) in methylene chloride (300 ml) was added N,N-dimethylaniline (36.2 g) under cooling in an ice bath at 5° C. To the solution was added portionwise 2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochloride (syn isomer) (16.2 g) below 11° C. and the mixture was stirred for 45 minutes at 5° C. The reaction mixture was diluted with a mixed solvent of methylene chloride (100 ml) and water (200 ml) and adjusted to pH 2 with 1N hydrochloric acid. The organic layer was separated out, washed with water, dried over magnesium sulfate and evaporated to dryness. The residue was triturated in diethyl ether to give diphenylmethyl 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (32.4 g), mp 120° to 125° C. (dec.).

후처리

  1. customThe organic layer was separated out
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue was triturated in diethyl ether

출처 및 근거

ORD 기록
ord-a11c7bfbbb7e41bb9ba9a637defe5c84
출처 데이터셋
uspto-grants-1985_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04521413

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