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

HRID 1946471Notes

Reaction equation

HRID 1946471 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[CH:25]([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[CH:25]([CH3:27])[CH3:26])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58460173Ethyl [3-[(4-chlorophenyl)methyl]-2-(1-methylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]acetate

Product 1

HCID 46829878[3-[(4-Chlorophenyl)methyl]-2-(1-methylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]acetic acidYield 60.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 5 (94 mg) was dissolved in methanol (2 ml) and treated with sodium hydroxide, 2 M aq. (2 ml). The RM was left in solution for 1 hour. The RM was concentrated under vacuum. The residue was purified by MDAP (Method A). The desired fractions were combined and concentrated under nitrogen blowdown to give the title compound (53 mg). LC/MS MH+ 361, Rt 1.63 min (5 minute run).

Workup

  1. concentrationThe RM was concentrated under vacuum
  2. customThe residue was purified by MDAP (Method A)
  3. concentrationconcentrated under nitrogen

Sources & evidence

ORD record
ord-7a4dcfce619648778a684c1ef9d6baf5
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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