trans-3-(3-Cyano-phenylcarbamoyl)-4-(3-methoxycarbonyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester → trans-3-(3-Carboxy-phenyl)-4-(3-cyano-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1524290Notes

Reaction equation

HRID 1524290 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([O:21]C)=[O:20])[CH:14]=2)[C@H:10]([C:23](=[O:33])[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[N:32])[CH:26]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@@H:10]([C:23](=[O:33])[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[N:32])[CH:26]=2)[C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([OH:21])=[O:20])[CH:14]=2)[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68089439trans-3-(3-Cyano-phenylcarbamoyl)-4-(3-methoxycarbonyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68089451trans-3-(3-Carboxy-phenyl)-4-(3-cyano-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 88.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

Add to a solution of trans-3-(3-cyano-phenylcarbamoyl)-4-(3-methoxycarbonyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.20 g, 0.44 mmol) in MeOH (3 mL), sodium hydroxide as a 10% aqueous solution (0.40 mL, 1.00 mmol). Heat the mixture to 50° C. for 30 min then cool to room temperature and remove the MeOH under reduced pressure. Dilute the mixture with water and adjust the pH to approximately pH 5 by the addition of a 2 N solution of hydrochloric acid causing a solid to precipitate from solution. Collect the formed solid by filtration, wash with water and dry on the filter pad to provide 0.17 g of trans-3-(3-carboxy-phenyl)-4-(3-cyano-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a powder.

Workup

  1. temperaturethen cool to room temperature
  2. customremove the MeOH under reduced pressure
  3. additionDilute the mixture with water
  4. additionby the addition of a 2 N solution of hydrochloric acid causing a solid
  5. customto precipitate from solution
  6. customCollect the formed solid
  7. filtrationby filtration
  8. washwash with water
  9. customdry on the filter pad

Sources & evidence

ORD record
ord-0cd9da2582c242d182e65580eb0ec339
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

Loading…