Sodium Hydroxide → HCID 68284315, compound

HRID 1527356Notes

Reaction equation

HRID 1527356 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[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:4].[OH-].[Na+]>CO>[C:23]([O:22][C:20]([N:6]1[CH2:7][C@@H:8]([N:10]([CH3:19])[C:11]([O:13][CH2:14][C:15]([Cl:18])([Cl:17])[Cl:16])=[O:12])[CH2:9][C@H:5]1[C:3]([OH:4])=[O:2])=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68283260HCID 68283260, compound

Product 1

HCID 68284315HCID 68284315, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ((2S,4S)-4-[methyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (360 mg, 0.83 mmol) in MeOH (20 mL) was added aq. 1N NaOH (1.66 mL, 1.66 mmol). The reaction was stirred at RT for 16 h then was concentrated. The residue was acidified with aq 2N HCl to pH 3, extracted with EtOAc (2×25 mL). The organic phases were joined, dried over Na2SO4, filtered and concentrated. The crude residue was used without further purification in the next step. MS (UPLC): 421 [M+H]+, 419 [M−H]−; tR (HPLC conditions f): 1.00 min.

Workup

  1. concentrationthen was concentrated
  2. extractionextracted with EtOAc (2×25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was used without further purification in the next step
  7. custom1.00 min.

Sources & evidence

ORD record
ord-a25dd6429d6540c3bbd2e4a5c63b1919
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…