Ethyl bromoacetate → 1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-ethoxycarbonylmethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine

HRID 458913노트

반응식

HRID 458913 반응식
[O:1]=[S:2]1(=[O:27])[C:8]2[CH:9]=[C:10]([OH:14])[C:11]([Br:13])=[CH:12][C:7]=2[N:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:5][C:4]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:21][CH3:22])[CH2:3]1.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C(=O)([O-])[O-].[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC#N>[O:27]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:14][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:11]([Br:13])=[CH:12][C:7]=2[N:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:5][C:4]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:21][CH3:22])[CH2:3]1

참가 물질

6

반응물 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 98250801,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepine

생성물 1

HCID 223931181,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-ethoxycarbonylmethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine수율 95.2%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6342Acetonitrile용매

실험 절차

A mixture of 1,1-dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (WO 96/16051; 0.3 g), ethyl bromoacetate (0.14 g), sodium carbonate (0.3 g), tetrabutylammonium bromide (0.02 g) in MeCN (10 ml) were refluxed for 4 hours. The solvent was removed under reduced pressure. The residue was partitioned, between DCM/H2O and the organic layer was separated. The solvent was evaporated and the residue was purified by chromatography (DCM/EtOAc, 90:10) to give the title compound 0.34 g (95%). NMR (500 MHz) 0.7–0.9 (m, 6H), 1.0–1.8 (m, 11H), 3.2 (m, 2H), 3.6–3.8 (brs, 2H), 4.3 (q, 2H), 4.7 (s, 2H), 7.0–7.1 (m, 3H), 7.15 (s, 1H), 7.3 (m, 2H), 7.4 (s, 1H).

후처리

  1. temperaturewere refluxed for 4 hours
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was partitioned, between DCM/H2O
  4. customthe organic layer was separated
  5. customThe solvent was evaporated
  6. customthe residue was purified by chromatography (DCM/EtOAc, 90:10)

출처 및 근거

ORD 기록
ord-90a33a27ceff47788a0013de59233911
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192945B2

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