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

HRID 1946476Notes

Reaction equation

HRID 1946476 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]3[CH:15]([C:20](C(OCC)=O)(C(OCC)=O)[C:21]([O:23]CC)=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][C:13]=3[N:12]=[C:11]2[CH:36]([CH3:38])[CH3:37])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+]>C(O)C>[NH3:10].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]3[CH:15]([CH2:20][C:21]([OH:23])=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][C:13]=3[N:12]=[C:11]2[CH:36]([CH3:38])[CH3:37])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58460159Triethyl [3-[(3,4-dichlorophenyl)methyl]-2-(1-methylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]methanetricarboxylate

Product 1

HCID 67435460[3-[(3,4-Dichlorophenyl)methyl]-2-(1-methylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]acetic acid ammonia saltYield 132.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Intermediate 9 (435 mg) and Sodium hydroxide, 2M aq (2.3 mL) in Ethanol (6 mL) was stirred at RT for 5 mins and then at 80° C. for 3 hr. The solvent was concentrated under vacuum, the residue suspended in acetic acid (6.00 mL) and heated at 120° C. for 2 hr. The solvent was removed under vacuum and the residue was purified by reverse phase chromatography using acetonitrile water with an ammonium carbonate modifier. The desired fractions were combined and concentrated under vacuum to give a white solid (210 mg). LC/MS MH+ 395, Rt 2.10 min (5 minute run).

Workup

  1. waitat 80° C. for 3 hr
  2. concentrationThe solvent was concentrated under vacuum
  3. temperatureheated at 120° C. for 2 hr
  4. customThe solvent was removed under vacuum
  5. customthe residue was purified by reverse phase chromatography
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-67c14a6356674e8c82aad2628182d589
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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