Acetyl chloride → Z-Hse(Ac)-OH

HRID 651836

反応式

HRID 651836 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 11833323Z-Hse(Ac)-OH収率 67.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-436e184255444bcf8e6098e637b9f9bb
出典データセット
uspto-grants-2001_08
特許番号
US06281364B1

関連ノート

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