Allyl chloroformate → (R)-2-(allyloxycarbonylamino)-3-benzyloxy-1-propanol

HRID 1953347노트

반응식

HRID 1953347 반응식
[NH2:1][C@@H:2]([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4].Cl[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:18]([O:17][C:15]([NH:1][C@@H:2]([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4])=[O:16])[CH:19]=[CH2:20]

참가 물질

5

반응물 3

HCID 18052Allyl chloroformateHCID 516892Sodium BicarbonateHCID 141184082-Amino-3-(benzyloxy)propan-1-ol

생성물 1

HCID 53805095(R)-2-(allyloxycarbonylamino)-3-benzyloxy-1-propanol수율 94.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of (R)-2-amino-3-benzyloxy-1-propanol (5 g, 27.6 mmol) in CH2Cl2 (250 mL) was treated with allyl chloroformate (3.2 mL, 30 mmol) and saturated aqueous NaHCO3 (250 mL) for 18 h. The organic layer was separated and concentrated in vacuo. Purification by chromatography eluting with 30% EtOAc/hexanes afforded 6.9 g (94%) of (R)-2-(allyloxycarbonylamino)-3-benzyloxy-1-propanol as an amorphous solid: 1H NMR (CDCl3) δ2.56 (br s, 1 H), 3.69 (m, 3 H), 3.88 (m, 2 H), 4.54 (s, 2 H), 4.58 (d, 2 H, J=5.6 Hz), 5.23 (dd, 1 H, J=10.4, 1.1 Hz), 5.33 (dd, 1 H, J=17.1, 1.1 Hz), 5.42 (m, 1 H), 5.93 (m, 1 H), 7.35 (m, 5 H).

후처리

  1. customThe organic layer was separated
  2. concentrationconcentrated in vacuo
  3. customPurification by chromatography
  4. washeluting with 30% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-559bb48e1c0e42a3a37c3add6457355f
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06113918

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