Sodium Hydroxide → HCID 67547155, compound

HRID 490582Notes

Reaction equation

HRID 490582 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([N:10]([CH3:19])[C:11]([O:13][CH2:14][C:15]([Cl:18])([Cl:17])[Cl:16])=[O:12])[CH2:7][N:6]1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:4].[OH-].[Na+]>C1COCC1.CO.O>[CH2:20]([N:6]1[CH2:7][CH:8]([N:10]([CH3:19])[C:11]([O:13][CH2:14][C:15]([Cl:18])([Cl:16])[Cl:17])=[O:12])[CH2:9][CH:5]1[C:3]([OH:4])=[O:2])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 57674236HCID 57674236, compound

Product 1

HCID 67547155HCID 67547155, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4S)-1-benzyl-4-[methyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester in THF and methanol is added NaOH in water, and the reaction mixture is stirred overnight, and extracted with EA. The aqueous solution is acidified to ph 5-6 and extracted with EA. The organic phase is washed, dried and concentrated to give 1-benzyl-4-[methyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-2-carboxylic acid (28).

Workup

  1. extractionextracted with EA
  2. extractionextracted with EA
  3. washThe organic phase is washed
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a9bd565a6e0a45bf999ac9063fe0fde2
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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