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

HRID 53115

반응식

HRID 53115 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8cdb307b27bc454aa7617a7fccba9753
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618792

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