Potassium Carbonate → Isobutyloxycarbonyl-cyclohexylglycine

HRID 1295626Notes

Reaction equation

HRID 1295626 reaction equation
Cl.[CH:2]1([NH:8][CH2:9][C:10]([OH:12])=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([O:23][C:24](Cl)=[O:25])[CH:20]([CH3:22])[CH3:21]>C(#N)C.O>[CH2:19]([O:23][C:24]([N:8]([CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)[CH2:9][C:10]([OH:12])=[O:11])=[O:25])[CH:20]([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 62365Isobutyl chloroformateHCID 122207422-(Cyclohexylamino)acetic acid hydrochloride

Product 1

HCID 67159202Isobutyloxycarbonyl-cyclohexylglycineYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of the commercially available cyclohexylglycine hydrochloride (15 g, 77.4 mmol) in acetonitrile (320 ml) and water (320 ml) was added potassium carbonate. Isobutylchloroformate (11.1 ml, 85.1 mmol) was added to the clear solution over 15 minutes and the reaction was stirred for 17 hours. The acetonitrile was removed under reduced pressure and the remaining aqueous layer was extracted twice with ether (100 ml). The aqueous layer was then acidified to pH 1 with 6N hydrochloric acid and extracted with dichloromethane (3×300 ml). The organic layer was dried over sodium sulfate, filtered and concentrated to yield 18.64 g (94%) product as a white solid.

Workup

  1. customThe acetonitrile was removed under reduced pressure
  2. extractionthe remaining aqueous layer was extracted twice with ether (100 ml)
  3. extractionextracted with dichloromethane (3×300 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4379e80e1fe9497995607e39cfd01486
Source dataset
uspto-grants-2007_07
Patent number
US07244721B2

Reaction notes

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