(R)-2-(6-Chloro-4'-ethoxycarbonyl-biphenyl-3-ylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester → (R)-2-(4'-Carboxy-6-chloro-biphenyl-3-ylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1678515Notes

Reaction equation

HRID 1678515 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[C:14](=[O:34])[NH:15][C:16]1[CH:17]=[C:18]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([O:31]CC)=[O:30])=[CH:25][CH:24]=2)[C:19]([Cl:22])=[CH:20][CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[OH-].[Na+].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[C:14](=[O:34])[NH:15][C:16]1[CH:17]=[C:18]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([OH:31])=[O:30])=[CH:27][CH:28]=2)[C:19]([Cl:22])=[CH:20][CH:21]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67372169(R)-2-(6-Chloro-4'-ethoxycarbonyl-biphenyl-3-ylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67373093(R)-2-(4'-Carboxy-6-chloro-biphenyl-3-ylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

(R)-2-(6-Chloro-4′-ethoxycarbonyl-biphenyl-3-ylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (306 mg) in 2M NaOH (6 ml) and ethanol (10 ml) was stirred at room temp for 18 h. The ethanol was then evaporated and the residue acidified with HCl. The resulting off-white solid was collected by filtration and dried (143 mg). Material used without purification in next step.

Workup

  1. customThe ethanol was then evaporated
  2. filtrationThe resulting off-white solid was collected by filtration
  3. customdried (143 mg)
  4. customMaterial used without purification in next step

Sources & evidence

ORD record
ord-3302571412d542c4b80f0d5e6392301b
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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