Sodium Hydroxide → HCID 57674238, compound

HRID 490651Notes

Reaction equation

HRID 490651 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][C@@H:8]([N:10]([CH3:19])[C:11]([O:13][CH2:14][C:15]([Cl:18])([Cl:16])[Cl:17])=[O:12])[CH2:9][C@H: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 57674238HCID 57674238, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4S)-1-benzyl-4-[methyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester (6.4 mmol) in 18 mL of THF and 12 mL of methanol was added a solution of NaOH (12.8 mmol) in 10 mL water, and the reaction mixture was stirred overnight. The solution was diluted with 40 mL of water and extracted with 20 mL of EA. The aqueous layer was separated and acidified with 2N HCl to PH=5-6. Then the solution was extracted with EA (3×40 mL). The combined organic layers were washed by brine (20 mL), dried over Na2SO4, and concentrated to give 2.6 g of title product in 91% yield. MS m/e=410.4 [M+H]+.

Workup

  1. extractionextracted with 20 mL of EA
  2. customThe aqueous layer was separated
  3. extractionThen the solution was extracted with EA (3×40 mL)
  4. washThe combined organic layers were washed by brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-44cc7d26b1f741fc8344a7a9af0a560f
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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