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

HRID 1678512Notes

Reaction equation

HRID 1678512 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13](=[O:33])[NH:14][C:15]1[CH:16]=[C:17]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([O:30]CC)=[O:29])=[CH:24][CH:23]=2)[C:18]([Cl:21])=[CH:19][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[OH-].[Na+].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13](=[O:33])[NH:14][C:15]1[CH:16]=[C:17]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([OH:30])=[O:29])=[CH:26][CH:27]=2)[C:18]([Cl:21])=[CH:19][CH:20]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67374244(R)-2-(6-Chloro-4'-ethoxycarbonyl-biphenyl-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67372818(R)-2-(4'-Carboxy-6-chloro-biphenyl-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

(R)-2-(6-Chloro-4′-ethoxycarbonyl-biphenyl-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (985 mg) in 2M NaOH (5 ml) and ethanol (7 ml) was stirred at room temp for 18 h. The ethanol was then evaporated and the residue acidified with HCl. The resulting yellow solid was collected by filtration and dried (672 mg). Material used without purification in next step.

Workup

  1. customThe ethanol was then evaporated
  2. filtrationThe resulting yellow solid was collected by filtration
  3. customdried (672 mg)
  4. customMaterial used without purification in next step

Sources & evidence

ORD record
ord-196503e2f3d94db0be2a39d0d2a5abb7
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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