Sodium Hydroxide → HCID 66971194, compound

HRID 1361303Notes

Reaction equation

HRID 1361303 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([C:22](=[O:31])[C:23]([CH3:30])([CH3:29])[CH2:24][O:25]C(=O)C)[CH:14]2[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]2)[CH2:10][C@@:9]1(C)[C:32]([O-:34])=[O:33])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+]>CO.O>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH:14]2[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]2)[C:22](=[O:31])[C:23]([CH3:30])([CH3:29])[CH2:24][OH:25])[CH2:10][C@H:9]1[C:32]([OH:34])=[O:33])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86636641HCID 86636641, compound

Product 1

HCID 66971194HCID 66971194, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-BOC-2-methyl-(2S,4S)-4-{[3-(acetyloxy)-2,2-dimethylpropanoyl](4,4-methylcyclohexyl)amino}pyrrolidine-2-carboxylate (1.02 g, 2.05 mmol) prepared in Step A in methanol (10 ml) and water (10 ml), was added NaOH (246 mg, 6.15 mmol), and stiffed for 12 h. After the reaction finished, the reaction solution was concentrated in vacuo, acidified with 1N HCl, and extracted with EtOAc. The organic extracts were washed with 1N HCl, dried MgSO4, and concentrated in vacuo to give the title compound (0.85 g, 95%).

Workup

  1. concentrationthe reaction solution was concentrated in vacuo
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed with 1N HCl, dried MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9cbf6ee02a224afe8f03f9dab3c40482
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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