Benzyl chloroformate → N-benzyloxy-carbonyl-O-acetyl-L-homoserine

HRID 2298544Notes

Reaction equation

HRID 2298544 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:13](=[O:16])([O-])O.[Na+].ClC([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O>O>[CH2:22]([O:21][NH:9][C@H:8]([C:10]([OH:12])=[O:11])[C:7](=[C:13]=[O:16])[CH2:6][O:5][C:2](=[O:4])[CH3:3])[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 86583740N-benzyloxy-carbonyl-O-acetyl-L-homoserineYield 93.8%

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-benzyloxy-carbonyl-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-2efa141aa8bd461bb4eeb9d94084e58b
Source dataset
uspto-grants-2002_12
Patent number
US06492541B2

Reaction notes

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