(+)-Styrene oxide → (R)-4-[2-(N-benzyl-N-(2-hydroxy-2-phenylethyl)amino)ethoxy]phenylacetamide

HRID 1647853

반응식

HRID 1647853 반응식
[CH2:1]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH2:21])=[O:20])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]1[O:30][C@@H:23]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(O)C>[CH2:1]([N:8]([CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([NH2:21])=[O:20])=[CH:16][CH:17]=1)[CH2:22][C@H:23]([OH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 114705(+)-Styrene oxideHCID 189972424-(Benzylaminoethoxy)-phenylacetamide

생성물 1

HCID 10024191(R)-4-[2-(N-benzyl-N-(2-hydroxy-2-phenylethyl)amino)ethoxy]phenylacetamide수율 64.8%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A mixture of 4-[2-(benzylamino)ethoxy]phenylacetamide (OLS 2135678) (14.0 g), (R)-styrene oxide (5.92 g) and propan-2-ol (200 ml) was heated under reflux for 72 hours. The mixture was cooled and the solvent evaporated under reduced pressure. The residue was purified by dry, flash column chromatography. Elution with 10% methanol in dichloromethane gave (R)-4-[2-(N-benzyl-N-(2-hydroxy-2-phenylethyl)amino)ethoxy]phenylacetamide as an oil (12.9 g). This reaction may also be performed in t-amyl alcohol under reflux.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 72 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent evaporated under reduced pressure
  5. customThe residue was purified
  6. customby dry
  7. washElution with 10% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-9e8fabcde85d417a8cbdf5fcc38219a9
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05434184

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