Potassium Carbonate → 3-(Tert-Butyldisulfanyl)-2-(Isobutoxycarbonylamino)Propanoic Acid

HRID 923719Notes

Reaction equation

HRID 923719 reaction equation
[C:1]([S:5][S:6][CH2:7][C@@H:8]([C:10]([OH:12])=[O:11])[NH2:9])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21]>CC#N.O>[C:1]([S:5][S:6][CH2:7][CH:8]([NH:9][C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21])[C:10]([OH:12])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 62365Isobutyl chloroformateHCID 7006457s-tert-Butylmercapto-L-cysteine

Product 1

HCID 871033123-(Tert-Butyldisulfanyl)-2-(Isobutoxycarbonylamino)Propanoic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To S-tert-butylmercapto-L-cysteine (10 g, 47.8 mmol) in CH3CN (40 mL) was added K2CO3 (16.5 g, 119.5 mmol) in H2O (20 mL). After stirring for 15 minutes, iso-butyl chloroformate (9.4 mL, 72 mmol) was injected slowly. The reaction was allowed to run for 3 hours. The white solid was filtered through Celite; the filtrate was concentrated to remove CH3CN. The residue was dissolved in ethyl acetate (200 mL), washed with 1N HCl (40 ml×3), brine (40×1), dried over Na2SO4. The title compound was obtained after chromatography (5% MeOH/DCM).

Workup

  1. waitto run for 3 hours
  2. filtrationThe white solid was filtered through Celite
  3. concentrationthe filtrate was concentrated
  4. customto remove CH3CN
  5. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  6. washwashed with 1N HCl (40 ml×3), brine (40×1)
  7. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-34207af3502348d3a7feef1a9b495653
Source dataset
uspto-grants-2016_03
Patent number
US09278987B2

Reaction notes

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