Benzyl chloroformate → Z-Hse(Ac)-OH

HRID 651835Notes

Reaction equation

HRID 651835 reaction equation
Cl.[C:2]([O:5][CH2:6][CH2:7][C@@H:8]([C:10]([OH:12])=[O:11])[NH2:9])(=[O:4])[CH3:3].C(=O)([O-])O.[Na+].Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>O>[CH2:22]([O:21][C:19]([NH:9][C@H:8]([C:10]([OH:12])=[O:11])[CH2:7][CH2:6][O:5][C:2](=[O:4])[CH3:3])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 45038083O-Acetyl-L-homoserine hydrochloride

Product 1

HCID 11833323Z-Hse(Ac)-OHYield 93.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

19.8 g (0.10 mol) of O-acetyl-L-homoserine hydrochloride are dissolved in 200 ml of water, and 35.0 g (0.42 mol) of sodium hydrogen carbonate are added at 0° C. 19.2 g (0.11 mol) of benzyl chloroformate are then added and stirring is carried out for 3 hours at room temperature. The mixture is then extracted twice using 100 ml of methyl isobutyl ketone each time, and the aqueous phase is adjusted to pH=2 using concentrated hydrochloric acid and extracted twice using 150 ml of methyl isobutyl ketone (MIBK) each time. The combined organic phases are washed with 50 ml of saturated sodium chloride solution and concentrated in vacuo. 27.5 g (93%) of N-benzyloxycarbonyl-O-acetyl-L-homoserine are obtained in the form of a colourless oil.

Workup

  1. extractionThe mixture is then extracted twice
  2. extractionextracted twice
  3. washThe combined organic phases are washed with 50 ml of saturated sodium chloride solution
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e1ddcd51cd24542ac0eb4fbf6e8cbff
Source dataset
uspto-grants-2001_08
Patent number
US06281364B1

Reaction notes

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