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Sulfamic Acid → Trimethylsilyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate-1-oxide

HRID 1902921
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HRID 1902921 반응식
[CH3:1][Si:2]([CH3:8])([CH3:7])NC(=O)C.[C:9]([NH:17][CH:18]1[C:30](=[O:31])[N:20]2[C:21]([C:27]([OH:29])=[O:28])=[C:22]([CH3:26])[CH2:23][S:24](=[O:25])[C@H:19]12)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.NS(O)(=O)=O.[Br:37]N1C(=O)CCC1=O>ClCCl>[C:9]([NH:17][CH:18]1[C:30](=[O:31])[N:20]2[C:21]([C:27]([O:29][Si:2]([CH3:8])([CH3:7])[CH3:1])=[O:28])=[C:22]([CH2:26][Br:37])[CH2:23][S:24](=[O:25])[C@H:19]12)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
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참가 물질

6

반응물 4

HCID 5987Sulfamic AcidHCID 25989Acetamide, N-(trimethylsilyl)-HCID 67184N-bromobutanimideHCID 704647027-Benzamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide

생성물 1

HCID 70463851Trimethylsilyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate-1-oxide수율 48%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

208 mg of N-trimethylsilylacetamide (1.59 mmoles) were added to a suspension of 383 mg (1.14 mmoles) of 7-benzamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide in 25 ml of dichloromethane, and after stirring for 11/2 hours at room temperature, a clear solution was obtained, which was diluted with dichloromethane to 50 ml. 200 mg of amidosulfonic acid (1.04 mmoles) were added thereto and the mixture was cooled in an ice-bath. Bromination was carried out in half an hour using 310 mg (1.74 mmoles) of N-bromosuccinimide as the brominating agent to obtain a 48% yield of trimethylsilyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate-1-oxide.

후처리

  1. customa clear solution was obtained
  2. temperaturethe mixture was cooled in an ice-bath
  3. waitBromination was carried out in half an hour

출처 및 근거

ORD 기록
ord-e56895226ad148ef9fa9bdfb31a824ae
출처 데이터셋
uspto-grants-1982_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04366315

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