Lithium Hydroxide → 4-[(R)-3-(4'-Carboxy-3,5-dichloro-biphenyl-4-ylmethyl)-2-oxo-pyrrolidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1171154Notes

Reaction equation

HRID 1171154 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C@@H:16]([CH2:19][C:20]3[C:25]([Cl:26])=[CH:24][C:23]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([O:35]C)=[O:34])=[CH:29][CH:28]=4)=[CH:22][C:21]=3[Cl:37])[C:15]2=[O:38])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C@@H:16]([CH2:19][C:20]3[C:21]([Cl:37])=[CH:22][C:23]([C:27]4[CH:28]=[CH:29][C:30]([C:33]([OH:35])=[O:34])=[CH:31][CH:32]=4)=[CH:24][C:25]=3[Cl:26])[C:15]2=[O:38])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 666715514-[(R)-3-(3,5-Dichloro-4'-methoxycarbonyl-biphenyl-4-ylmethyl)-2-oxo-pyrrolidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 666716484-[(R)-3-(4'-Carboxy-3,5-dichloro-biphenyl-4-ylmethyl)-2-oxo-pyrrolidin-1-yl]-piperidine-1-carboxylic acid tert-butyl esterYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of 4-[(R)-3-(3,5-Dichloro-4′-methoxycarbonyl-biphenyl-4-ylmethyl)-2-oxo-pyrrolidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Preparation 16) (0.4 g, 0.7 mmol) in THF (5 mL) with 1N aqueous LiOH (3.6 mL). Stir the reaction overnight at room temperature. Quench the reaction with 1N HCl and extract with EtOAc. Wash the organic with brine, dry over MgSO4, and filter. Remove the solvent to afford 0.37 g (96%) of desired product. MS (m/e): 569 (M+Na+).

Workup

  1. customthe reaction overnight at room temperature
  2. customQuench
  3. customthe reaction with 1N HCl
  4. extractionextract with EtOAc
  5. washWash the organic with brine
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customRemove the solvent

Sources & evidence

ORD record
ord-b9ef3053c82c43428c0160c2779a4116
Source dataset
uspto-grants-2010_11
Patent number
US07829582B2

Reaction notes

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