Lithium Hydroxide → HCID 67546799, compound

HRID 490623Notes

Reaction equation

HRID 490623 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:10]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[C:11]([O:13][CH2:14][C:15]([Cl:18])([Cl:17])[Cl:16])=[O:12])[CH2:7][N:6]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:4].[Li+].[OH-]>CO>[C:31]([O:30][C:28]([N:6]1[CH2:7][CH:8]([N:10]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[C:11]([O:13][CH2:14][C:15]([Cl:17])([Cl:16])[Cl:18])=[O:12])[CH2:9][CH:5]1[C:3]([OH:4])=[O:2])=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67546998HCID 67546998, compound

Product 1

HCID 67546799HCID 67546799, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[(2,4-difluoro-benzyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-1,2-dicarboxylicacid 1-tert-butyl ester 2-methyl ester (8 g, 14.7 mmol) in MeOH (50 ml) cooled to 0 degree was added LiOH (2.47 g, 58.8 mmol), and the mixture was stirred overnight. After removal of methanol, the residue was acidified with 2M HCl. The aqueous layer was extracted with EA, and the organic solution was dried and concentrated. The residue was purified by chromatography (PE:EA=3:1) on silica gel to afford the title product as yellow oil (3.5 g, 6.5 mmol). MS m/e=531.2 [M+H]+.

Workup

  1. customAfter removal of methanol
  2. extractionThe aqueous layer was extracted with EA
  3. customthe organic solution was dried
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (PE:EA=3:1) on silica gel

Sources & evidence

ORD record
ord-5663212d4d0640b59b579ca6fb51173e
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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