(S)-2-(4'-Ethoxycarbonyl-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl ester → (S)-2-(4'-Carboxy-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 1678503Notes

Reaction equation

HRID 1678503 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[C:12](=[O:36])[NH:13][C:14]1[CH:15]=[C:16]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([O:33]CC)=[O:32])=[CH:27][CH:26]=2)[C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:18][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[C:12](=[O:36])[NH:13][C:14]1[CH:15]=[C:16]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([OH:33])=[O:32])=[CH:27][CH:26]=2)[C:17]([O:20][C:21]([F:24])([F:22])[F:23])=[CH:18][CH:19]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67371803(S)-2-(4'-Ethoxycarbonyl-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67374213(S)-2-(4'-Carboxy-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl esterYield 86.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of (S)-2-(4′-Ethoxycarbonyl-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl ester (188 mg) in ethanol (15 ml) and sodium hydroxide (2M, 5 ml) was stirred at room temp for 18 h. The mixture was acidified and the ethanol evaporated. The residue was extracted with DCM and the dried extracts evaporated giving the crude acid as a pale orange gum (154 mg).

Workup

  1. customthe ethanol evaporated
  2. extractionThe residue was extracted with DCM
  3. customthe dried extracts evaporated

Sources & evidence

ORD record
ord-893b779fdab64a8d871c77a8bbf0f825
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

Loading…