Sodium Hydroxide → [3-[(4-Chlorophenyl)methyl]-2-(1,1-dimethylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]acetic acid

HRID 1946483Notes

Reaction equation

HRID 1946483 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([CH2:19][C:20]([O:22]CC)=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][C:12]=3[N:11]=[C:10]2[C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([CH2:19][C:20]([OH:22])=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][C:12]=3[N:11]=[C:10]2[C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58460191Ethyl[3-[(4-chlorophenyl)methyl]-2-(1,1-dimethylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]acetate

Product 1

HCID 58460190[3-[(4-Chlorophenyl)methyl]-2-(1,1-dimethylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]acetic acidYield 83.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 16 (22 mg) was dissolved in Methanol (1 ml) and treated with sodium hydroxide, 2M aq. (1 mL). The RM was left in solution for 1 hour. The residue was purified by MDAP (Method A). The desired fractions were combined and concentrated under nitrogen blowdown to give the title compound (17 mg). LC/MS MH+ 375, Rt 1.72 min (5 minute run).

Workup

  1. customThe residue was purified by MDAP (Method A)
  2. concentrationconcentrated under nitrogen

Sources & evidence

ORD record
ord-25c21ae17e7b4fd3b03b92583255d5a1
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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