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

HRID 1884775ノート

反応式

HRID 1884775 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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) δ 2.56 (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).

後処理

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

出典と根拠

ORDレコード
ord-697d25bf3e8546bf9d45a93682a988a2
出典データセット
uspto-grants-2004_07
特許番号
US06764840B2

反応ノート

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