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

HRID 1291558Notes

Reaction equation

HRID 1291558 reaction equation
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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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-chlorobenzoyl-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.

Workup

  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

Sources & evidence

ORD record
ord-82708e400c0c48348266a894eda2ff09
Source dataset
uspto-grants-1998_05
Patent number
US05753644

Reaction notes

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