Water → 5-carboxymethyl-7-chloro-1-[2-hydroxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

HRID 54759노트

반응식

HRID 54759 반응식
B(Br)(Br)Br.[C:5]([CH2:8][CH:9]1[C:15]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=2[N:13]([C:21](=[O:40])[C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])=[CH:24][C:23]=2[O:38]C)[CH2:12][CH2:11][CH2:10]1)([OH:7])=[O:6].O>ClCCl>[C:5]([CH2:8][CH:9]1[C:15]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=2[N:13]([C:21](=[O:40])[C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])=[CH:24][C:23]=2[OH:38])[CH2:12][CH2:11][CH2:10]1)([OH:7])=[O:6]

참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromideHCID 189172735-carboxymethyl-7-chloro-1-[2-methoxy-4-(2-chloro-benzoyl-amino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

생성물 1

HCID 189173835-carboxymethyl-7-chloro-1-[2-hydroxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine수율 93.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

9.1 ml of 98% boron tribromide was dropwise added, at -10° C. with stirring, to a solution of 10 g of 5-carboxymethyl-7-chloro-1-[2-methoxy-4-(2-chloro-benzoyl-amino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine dissolved in 400 ml of dichloromethane. The mixture was slowly returned to room temperature and stirred overnight at the same temperature. The reaction mixture was mixed with water, followed by extraction with dichloromethane. The extract was water-washed, then dried over anhydrous magnesium sulfate, and subjected to vacuum distillation to remove the solvent. The residue was purified by silica gel column chromatography to obtain 9.08 g of 5-carboxymethyl-7-chloro-1-[2-hydroxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine.

후처리

  1. customwas slowly returned to room temperature
  2. extractionfollowed by extraction with dichloromethane
  3. washwashed
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationsubjected to vacuum distillation
  6. customto remove the solvent
  7. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-8a61403d517d44ceb2f2c5afac5377c7
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622947

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