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Hydrochloric Acid → p-Nitrobenzyl alpha-[4-mercapto-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-hydroxyethylidene)acetate

HRID 971520
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HRID 971520 반응식
C1(COC([S:8][CH:9]2[N:12]([C:13](=[C:27]([OH:30])[CH2:28][Br:29])[C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C:11](=[O:31])[CH:10]2[NH:32][C:33](=[O:42])[CH2:34][O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=O)CC1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>CO>[SH:8][CH:9]1[N:12]([C:13](=[C:27]([OH:30])[CH2:28][Br:29])[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C:11](=[O:31])[CH:10]1[NH:32][C:33](=[O:42])[CH2:34][O:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 86735549p-Nitrobenzyl alpha-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-hydroxyethylidene)acetate

생성물 1

HCID 86735550p-Nitrobenzyl alpha-[4-mercapto-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-hydroxyethylidene)acetate수율 94.6%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

To a solution of p-nitrobenzyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate (281 mg) in methanol free methylene chloride (2.1 ml) is added aluminum chloride (220 mg) under ice cooling, and the mixture is stirred under argon atmosphere. After 35 minutes, the reaction mixture is poured into ice water containing 4N-hydrochloric acid (4 ml). stirred for 10 minutes, and is extracted with chloroform. The extract solution is washed with water, dried and evaporated to give p-nitrobenzyl α-[4-mercapto-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate (150 mg). Yellow foam. Yield: 94.6%. IR: vmaxCDCl3 3400, 1780, 1692, 1610, 1603 cm-1. NMR: δCDCl3 2.25d(10Hz)1H, 4.25d(2Hz), 4.58s2H, 5.20-5.37m4H, 6.84-8.24m9H, 12.1s1H.

후처리

  1. stirringstirred for 10 minutes
  2. extractionis extracted with chloroform
  3. washThe extract solution is washed with water
  4. customdried
  5. customevaporated

출처 및 근거

ORD 기록
ord-d5e467ff047f4bc996c15897d9201ddd
출처 데이터셋
uspto-grants-1979_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04160085

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