Benzyl chloroformate → (S)-2-(((Benzyloxy)carbonyl)amino)-3-cyclohexylpropanoic acid

HRID 1196463Notes

Reaction equation

HRID 1196463 reaction equation
Cl.[CH:2]1([CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:14]([O:21][C:22](Cl)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[OH-].[Na+].O1CCCC1>[CH2:14]([O:21][C:22]([NH:10][C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 23381533(S)-2-Amino-3-cyclohexylpropanoic acid hydrochloride

Product 1

HCID 14158015(S)-2-(((Benzyloxy)carbonyl)amino)-3-cyclohexylpropanoic acidYield 69%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent3×

Procedure

To a solution of 3-cyclohexylalanine, hydrochloride (4.75 , 22.8 mmol) in 2N sodium hydroxide (11.4 mL) were added at 0° C., simultaneously, a solution of benzylchloroformate (3.2 mL, 36 mmol) in tetrahydrofuran (10 mL) and 2N sodium hydroxide (11.4 mL). (The pH of the mixture was maintained around 9-10 by addition of 2N sodium hydroxide.) The mixture was stirred for 1.5 hours. The solution was washed with diethyl ether (3×20 mL). The aqueous phase was acidified to pH 2 with 3N aqueous hydrochloric acid and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over anhydrous magnesium sulphate. Filtration and removal of the solvent in vacuo left 4.80 g of the expected product (yellow oil, 69% yield).

Workup

  1. washThe solution was washed with diethyl ether (3×20 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulphate
  4. filtrationFiltration and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-e8614defd3404469aeb8615cf4130cb7
Source dataset
uspto-grants-1992_05
Patent number
US05114927

Reaction notes

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