Lithium Hydroxide → 1-Benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid

HRID 490593Notes

Reaction equation

HRID 490593 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:10]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])[CH2:7][N:6]1[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:4].[Li+].[OH-]>CO>[CH2:27]([N:6]1[CH2:7][CH:8]([N:10]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])[CH2:9][CH:5]1[C:3]([OH:4])=[O:2])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 675472001-Benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 675474701-Benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acidYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester (109 g, 4.13 mmol) in CH3OH (10 ml) was added LiOH (0.826 g, 20.65 mmol), and the solution was stirred overnight at rt. After removal of solvent, the residue was dissolved in water, acidified until PH=5, and then extracted by EA. The organic phase was washed with water (2×50 mL) and brine (40 mL), dried over anhydrous Na2SO4, and concentrated to afford the product 1-benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid 1.72 g (93%) as white solid. MS m/e=447.4 [M+H]+.

Workup

  1. customAfter removal of solvent
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted by EA
  4. washThe organic phase was washed with water (2×50 mL) and brine (40 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4c6d42b5cb734cf0b71652387805bc3f
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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