Hydrochloric Acid → [5-(2-Bromophenyl)-7-chloro-1-isobutyl-2-oxo-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl]acetic acid

HRID 1444833Notes

Reaction equation

HRID 1444833 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][N:6]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Br:19])[C:10]2[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:9]=2[CH:8]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:7]1=[O:29])C.[OH-].[Na+].Cl>C1COCC1.CO.O>[Br:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:11]1[CH2:12][N:6]([CH2:5][C:4]([OH:30])=[O:3])[C:7](=[O:29])[CH:8]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:9]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:10]1=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59025471Ethyl[5-(2-bromophenyl)-7-chloro-1-isobutyl-2-oxo-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl]-acetate

Product 1

HCID 59025465[5-(2-Bromophenyl)-7-chloro-1-isobutyl-2-oxo-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl]acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

185 mg of the compound from Example 14A (0.38 mol) are dissolved in 6 ml of THF/methanol (1:1) and 1 ml of 1 N sodium hydroxide solution is added. The reaction mixture is stirred at room temperature for 16 h. It is diluted with water and acidified with 2 N hydrochloric acid, and the mixture is extracted three times with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated in a rotary evaporator. 172 mg (99% of theory) of the title compound are obtained.

Workup

  1. extractionthe mixture is extracted three times with dichloromethane
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-6f54400eb722459fa7d10de3147f7a0c
Source dataset
uspto-grants-2010_02
Patent number
US07662956B2

Reaction notes

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