Triethylamine → (5R)-5,6-bis(nitrooxy)hexyl 1-chloroethyl carbonate

HRID 1361904노트

반응식

HRID 1361904 반응식
Cl[C:2]([O:4][CH:5]([Cl:7])[CH3:6])=[O:3].[N+:8]([O-:22])([O:10][CH2:11][C@H:12]([O:18][N+:19]([O-:21])=[O:20])[CH2:13][CH2:14][CH2:15][CH2:16][OH:17])=[O:9].C(N(CC)CC)C>C(Cl)Cl>[C:2](=[O:3])([O:4][CH:5]([Cl:7])[CH3:6])[O:17][CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]([O:18][N+:19]([O-:21])=[O:20])[CH2:11][O:10][N+:8]([O-:22])=[O:9]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 5213051-Chloroethyl chloroformateHCID 59556786(2R)-6-hydroxyhexane-1,2-diyl dinitrate

생성물 1

HCID 59370672(5R)-5,6-bis(nitrooxy)hexyl 1-chloroethyl carbonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1-Chloroethyl chloroformate (6.42 mL, 58.9 mmol) was added dropwise to a stirred solution of (2R)-6-hydroxyhexane-1,2-diyl dinitrate (12 g, 53.5 mmol) and triethylamine (8.95 mL, 64.2 mmol) in DCM (268 mL) at 0° C. After 2 h, the solution was washed with water, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 5-40% EtOAc/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 6.40 (q, J=6.0 Hz, 1H), 5.28 (ddd, J=13.0, 6.2, 3.0 Hz, 1H), 4.74 (dd, J=13.0, 3.0 Hz, 1H), 4.47 (dd, J=13.0, 6.5 Hz, 1H), 4.25-4.16 (m, 2H), 1.82 (d, J=6.0 Hz, 3H), 1.82-1.71 (m, 4H), 1.63-1.46 (m, 2H).

후처리

  1. washthe solution was washed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with 5-40% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-32a73ad621074bada1a5750b9600c100
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07880014B2

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