Acetyl chloride → Z-Hse(Ac)-OH

HRID 651836

반응식

HRID 651836 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 11833323Z-Hse(Ac)-OH수율 67.1%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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 isobutyl 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.

후처리

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

출처 및 근거

ORD 기록
ord-436e184255444bcf8e6098e637b9f9bb
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06281364B1

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