Acetyl chloride → O-Acetyl-L-homoserine hydrochloride

HRID 2298543Notes

Reaction equation

HRID 2298543 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5].[C:9]([Cl:12])(=[O:11])[CH3:10]>C(O)(=O)C>[ClH:12].[C:9]([O:5][CH2:4][CH2:3][C@@H:2]([C:6]([OH:8])=[O:7])[NH2:1])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 12647L-Homoserine2×

Product 1

HCID 45038083O-Acetyl-L-homoserine hydrochlorideYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

72 g (0.60 mol) of L-homoserine are added in portions to a solution of 500 ml of acetic acid and 500 ml of acetyl chloride while cooling at <30° C. After 2 hours' stirring, no homoserine can be detected by TLC. The precipitate is filtered off with suction and washed with acetic acid. Drying in vacuo yields 90.1 g (75%) of O-acetyl-L-homo-serine hydrochloride.

Workup

  1. temperaturewhile cooling at <30° C
  2. filtrationThe precipitate is filtered off with suction
  3. washwashed with acetic acid
  4. customDrying in vacuo

Sources & evidence

ORD record
ord-3139e9aa737e400ca1654b114263f0ff
Source dataset
uspto-grants-2002_12
Patent number
US06492541B2

Reaction notes

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