Acetone → (4S)-4-{[(tert-butoxy)carbonyl]amino}-5-methylhexanoic acid

HRID 491906Notes

Reaction equation

HRID 491906 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C@H:9]1[CH:14]([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)=[O:19].[OH-].[Na+].S(=O)(=O)(O)[O-].[Na+]>O>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH:14]([CH3:16])[CH3:15])[CH2:10][CH2:11][C:12]([OH:19])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 516919Sodium BisulfateHCID 60054970tert-Butyl (S)-2-isopropyl-5-oxopyrrolidine-1-carboxylate

Product 1

HCID 57678353(4S)-4-{[(tert-butoxy)carbonyl]amino}-5-methylhexanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2 L, one-necked flask (equipped with a magnetic stir bar and a nitrogen inlet) was charged with (S)-2-isopropyl-5-oxo-pyrrolidine-1-carboxylic acid, tert-butyl ester prepared in Step C above (77.4 g, 0.341 mol) and acetone (260 mL). To this solution was added 1M aqueous sodium hydroxide (408 mL, 0.408 mol), and the reaction mixture was stirred 30 minutes. The acetone was removed in vacuo and the resulting aqueous slurry was acidified, with vigorous stirring, by addition of solid sodium bisulfate (55 g, 0.45 mol) and diluted to 1 L with deionized water. The slurry was stirred for 2 h and the resulting white solid was collected by filtration, washed with deionized water, and dried in a vacuum oven to yield the product as a white solid.

Workup

  1. customA 2 L, one-necked flask (equipped with a magnetic stir bar and a nitrogen inlet)
  2. customThe acetone was removed in vacuo
  3. stirringThe slurry was stirred for 2 h
  4. filtrationthe resulting white solid was collected by filtration
  5. washwashed with deionized water
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-0508da52b5e948d08766fca28170a466
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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