Acetyl chloride → Z-Hse(Ac)-OH

HRID 2298545Notes

Reaction equation

HRID 2298545 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH2:13][CH2:14][OH:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O-])(=[O:21])[CH3:20].[Na+].C(Cl)(=O)C>C(O)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH2:13][CH2:14][O:15][C:19](=[O:21])[CH3:20])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 489187Cbz-L-HomoserineHCID 517045Sodium Acetate

Product 1

HCID 11833323Z-Hse(Ac)-OHYield 67.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.27 g (5 mmol) of N-benzyloxycarbonyl-L-homoserine are dissolved in 5 ml of acetic acid, and 0.41 g (5 mmol) of sodium acetate is added. 1.19 g (15 mmol) of acetyl chloride are then added and stirring is carried out for one hour. The acetic acid and the excess acetyl chloride are removed in vacuo, the residue is taken up in 30 ml of methyl isobutyl ketone and 30 ml of water, and the pH is adjusted to 8 using 50% sodium hydroxide solution. The aqueous phase is separated off, adjusted to pH=2 using hydrochloric acid and extracted using 30 ml of methyl iso-butyl ketone. Concentration of the organic phase in vacuo yields 0.99 g (67%) of N-benzyloxycarbonyl-O-acetyl-L-homoserine in the form of a colourless oil.

Workup

  1. customThe acetic acid and the excess acetyl chloride are removed in vacuo
  2. customThe aqueous phase is separated off
  3. extractionextracted

Sources & evidence

ORD record
ord-2287ea4641374f2ebe7832b41af203fa
Source dataset
uspto-grants-2002_12
Patent number
US06492541B2

Reaction notes

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