Acetone Cyanohydrin → ((S)-2-Cyano-2-hydroxy-1-isopropyl-ethyl)-carbamic acid benzyl ester

HRID 53115

反応式

HRID 53115 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH:16]=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([N:20](CC)CC)C.CC(C)(O)C#N>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH:16]([OH:17])[C:18]#[N:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 11009915benzyl [(1S)-1-formyl-2-methylpropyl]carbamate

生成物 1

HCID 18648816((S)-2-Cyano-2-hydroxy-1-isopropyl-ethyl)-carbamic acid benzyl ester収率 143%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution containing N-benzyloxycarbonyl-L-valinal 22.2 g, 0.094 mol) in methylene chloride (500 mL) and triethylamine (5.81 g, 8.0 mL, 0.057 mol) was added acetone cyanohydrin (24.23 g, 26.0 mL, 0.2847 mol). The reaction was allowed to stir at room temperature overnight and then concentrated under reduced pressure. The residue was taken up into ether and washed with brine (3×). The solvent was removed under reduced pressure and purified by column chromatography (silica gel; 1:2 acetone:hexane) to give 21.38 g (86.6%) of 3-(S)-[(benzyloxycarbonyl)amino]-2-hydroxy-4-methylpentanenitrile as a pale yellow oil; TLC Rf =0.33 (silica gel; 1:2 acetone:hexane).

後処理

  1. concentrationconcentrated under reduced pressure
  2. washwashed with brine (3×)
  3. customThe solvent was removed under reduced pressure
  4. custompurified by column chromatography (silica gel; 1:2 acetone:hexane)

出典と根拠

ORDレコード
ord-8cdb307b27bc454aa7617a7fccba9753
出典データセット
uspto-grants-1997_04
特許番号
US05618792

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