Lithium Hydroxide → 4-[(Benzyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-1,2-dicarboxylicacid 1-tert-butyl ester

HRID 490576Notes

Reaction equation

HRID 490576 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][CH:23]=[CH:22][CH:21]=2)[C:11]([O:13][CH2:14][C:15]([Cl:18])([Cl:17])[Cl:16])=[O:12])[CH2:7][N:6]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:4].[Li+].[OH-]>CO>[C:29]([O:28][C:26]([N:6]1[CH2:7][CH:8]([N:10]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:11]([O:13][CH2:14][C:15]([Cl:16])([Cl:17])[Cl:18])=[O:12])[CH2:9][CH:5]1[C:3]([OH:4])=[O:2])=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 675466644-[(Benzyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-1,2-dicarboxylicacid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 675477354-[(Benzyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-1,2-dicarboxylicacid 1-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[(benzyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-1,2-dicarboxylicacid 1-tert-butyl ester 2-methyl ester in MeOH, cooled to 0 degree is added LiOH, and the mixture is stirred overnight. After removal of the solvent, the residue is acidified with HCl. The aqueous layer is extracted with EA, and the organic solution is dried, concentrated and purified to afford 4-[(benzyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-1,2-dicarboxylicacid 1-tert-butyl ester (20).

Workup

  1. customAfter removal of the solvent
  2. extractionThe aqueous layer is extracted with EA
  3. customthe organic solution is dried
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-cfe7702d6c4843d98a063c6bc7f4f16d
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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