Benzyl chloroformate → N-Cbz-D-leucine

HRID 2058638Notes

Reaction equation

HRID 2058638 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C@@H:13]([C:18]([OH:20])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16]>[OH-].[Na+].O>[NH:12]([C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C@@H:13]([C:18]([OH:20])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 439524D-Leucine

Product 1

HCID 7000099N-Cbz-D-leucine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

Benzyloxycarbonyl chloride (abbreviated Z-Cl hereafter) (65 ml) and 114 ml of 4 N NaOH were simultaneously added under agitation with ice-cooling to a solution of 50 g of D-Leu in 191 ml of 2 N NaOH and stirred for a further one hour. After the reaction mixture was diluted with one liter of distilled water, it was rinsed three times with 300 ml each of ethyl acetate. The aqueous layer was adjusted to pH 2.0 with 4 N HCl under cooling with ice. The oily material formed was extracted with ethyl acetate. The ethyl acetate extract, after being washed with a saturated solution of sodium chloride, was dehydrated over anhydrous sodium sulfate and then evaporated under reduced pressure to give 44 g of colorless, transparent syrup.

Workup

  1. washwas rinsed three times with 300 ml each of ethyl acetate
  2. temperatureunder cooling with ice
  3. customThe oily material formed
  4. extractionwas extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washafter being washed with a saturated solution of sodium chloride
  7. customevaporated under reduced pressure
  8. customto give 44 g of colorless, transparent syrup

Sources & evidence

ORD record
ord-7fa20181af6f4398a6cf13dd898c2cff
Source dataset
uspto-grants-1982_03
Patent number
US04318847

Reaction notes

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