L-Valine → HCID 36689750, compound

HRID 1291770Notes

Reaction equation

HRID 1291770 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].[NH2:9][C@H:10]([C:14]([OH:16])=[O:15])[CH:11]([CH3:13])[CH3:12]>[OH-].[Na+]>[CH2:5]([O:4][C:2]([NH:9][C@H:10]([C:14]([OH:16])=[O:15])[CH:11]([CH3:13])[CH3:12])=[O:3])[CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 6287L-ValineHCID 62365Isobutyl chloroformate

Product 1

HCID 36689750HCID 36689750, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

11.2 ml (85.3 mmol) of isobutyl chloroformate are added to a solution of 10 g (85.3 mmol) of (L)-valine in 100 ml of 2N sodium hydroxide solution and the solution is stirred at RT for 18 h. The reaction solution is washed with methylene chloride, acidified with 4N hydrochloric acid and extracted with methylene chloride. The organic extracts are washed with brine and filtered through cotton wadding to yield the title compound in the form of a colourless resin after concentration by evaporation. 1H-NMR (200 MHz, CD3OD): 0.95 (m, 12H), 1.9 (m, 1H), 2.15 (m, 1H), 3.85 (d, J=7 Hz, 2H), 4.05 (d broad, 1H).

Workup

  1. washThe reaction solution is washed with methylene chloride
  2. extractionextracted with methylene chloride
  3. washThe organic extracts are washed with brine
  4. filtrationfiltered through cotton wadding

Sources & evidence

ORD record
ord-5163ba21572c475ba0b4b492d182624a
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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