Sulfamic Acid → Trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide

HRID 1902910노트

반응식

HRID 1902910 반응식
[CH3:1][C:2]1[CH2:3][S:4](=[O:24])[C@@H:5]2[CH:12]([NH:13][C:14](=[O:22])[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11](=[O:23])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].[CH3:25][Si:26]([CH3:32])([CH3:31])NC(=O)C.NS(O)(=O)=O.[Br:38]N1C(=O)CCC1=O>ClCCl>[CH3:25][Si:26]([CH:3]1[C:2]([CH2:1][Br:38])=[C:7]([C:8]([OH:10])=[O:9])[N:6]2[C:11](=[O:23])[CH:12]([NH:13][C:14](=[O:22])[CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C@H:5]2[S:4]1=[O:24])([CH3:32])[CH3:31]

참가 물질

6

반응물 4

HCID 5987Sulfamic AcidHCID 25989Acetamide, N-(trimethylsilyl)-HCID 67184N-bromobutanimideHCID 70485748HCID 70485748, 화합물

생성물 1

HCID 131712909Trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide수율 49%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

342 mg (0.98 mmole) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide were suspended in 25 ml of dichloromethane and the mixture was heated to refluxed 157 mg of N-trimethylsilylacetamide (1.20 mmoles) were added thereto and refluxing was continued for 3/4 hour. To the clear, colorless solution obtained, 50 mg of amidosulfonic acid (0.51 mmoles) were added and the mixture was diluted to 40 ml with dichloromethane. The ice-cooled solution was brominated in half an hour using 280 mg (1.57 mmoles) of N-bromosuccinimide as the brominating agent to obtain a yield of 49% of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide.

후처리

  1. temperaturethe mixture was heated
  2. additionwere added
  3. temperaturerefluxing
  4. waitwas continued for 3/4 hour
  5. customTo the clear, colorless solution obtained
  6. waitwas brominated in half an hour

출처 및 근거

ORD 기록
ord-28689f7c240a4199b041cded73d72031
출처 데이터셋
uspto-grants-1982_12
특허 번호
US04366315

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