1,2-Dichloroethane → (R)-N-(2-hydroxy-1-phenylethyl)pent-4-enamide

HRID 41074

반응식

HRID 41074 반응식
[C:1]([OH:7])(=O)[CH2:2][CH2:3][CH:4]=[CH2:5].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[C:22]1([C@H:28]([CH2:30][OH:31])[NH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[OH:31][CH2:30][C@H:28]([NH:29][C:1](=[O:7])[CH2:2][CH2:3][CH:4]=[CH2:5])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 611384-Pentenoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724025(R)-beta-aminophenethyl alcohol

생성물 1

HCID 67310926(R)-N-(2-hydroxy-1-phenylethyl)pent-4-enamide수율 64%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-pentenoic acid (2.55 mL, 25.0 mmol) in DMF (312 mL) cooled in an ice/water bath was added HOBt (3.37 g, 25.0 mmol) and EDC (4.79 g, 25.0 mmol) and the resulting solution was stirred for 30 min (R)-(−)-2-phenylglycinol (3.43 g, 25.0 mmol), iPr2NEt (17.8 mL, 100 mmol), and DMAP (0.305 g, 2.50 mmol) were subsequently added and the reaction mixture was stirred 16 h at which point LC-MS analysis indicated complete consumption of starting material. The reaction mixture was diluted with saturated NH4Cl and EtOAc and the layers separated. The aqueous layer was extracted 2× with EtOAc and the combined organic extracts were washed with 1 N HCl and brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified using silica gel chromatography (MeOH/CH2Cl2 gradient) to yield 3.5 g of product as a colorless oil in 64% yield. LRMS (M+H)+: 220.1.

후처리

  1. additionwere subsequently added
  2. customconsumption of starting material
  3. additionThe reaction mixture was diluted with saturated NH4Cl and EtOAc
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted 2× with EtOAc
  6. washthe combined organic extracts were washed with 1 N HCl and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified

출처 및 근거

ORD 기록
ord-b71a08174352423d9dc2227546fe4c2a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530456B2

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