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Sodium Carbonate → 1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-[1'-phenyl-1'-ethoxycarbonylmethoxy]-2,3,4,5-tetrahydro-1,5-benzothiazepine

HRID 458908
ノート
印刷プレビュー

反応式

HRID 458908 の反応式
Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C([O-])([O-])=O.[Na+].[Na+].[O:20]=[S:21]1(=[O:46])[C:27]2[CH:28]=[C:29]([OH:33])[C:30]([Br:32])=[CH:31][C:26]=2[N:25]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:24][C:23]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:40][CH3:41])[CH2:22]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC#N>[O:46]=[S:21]1(=[O:20])[C:27]2[CH:28]=[C:29]([O:33][CH:2]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:30]([Br:32])=[CH:31][C:26]=2[N:25]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:24][C:23]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:40][CH3:41])[CH2:22]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 97780Ethyl bromophenylacetateHCID 98250801,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepine

生成物 1

HCID 184424591,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-[1'-phenyl-1'-ethoxycarbonylmethoxy]-2,3,4,5-tetrahydro-1,5-benzothiazepine収率 94.2%

試薬・触媒・溶媒 2

HCID 74236
Tetrabutylammonium Bromide
触媒
HCID 6342Acetonitrile溶媒

実験手順

Ethyl α-bromophenylacetate (0.139 g), Na2CO3 (0.200 g) and tetrabutylammonium bromide (0.034 g) were added to a solution 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; 0.200 g, 0.442 mmol) in MeCN (6 ml). The suspension was heated under reflux overnight before the solvent was removed under reduced pressure. The crude product was extracted (DCM/H2O) and purified by flash chromatography (Hex:EtOAc-5:1) to give the title compound 0.256 g (94%) as a white solid. NMR 0.65–0.85 (m, 6H), 0.95–1.65 (m, 8H), 3.00–3.15 (m, 2H), 3.50–3.80 (m, 2H), 3.70–3.80 (2s, 3H), 5.60 (s, 1H), 5.65 (d, 1H) 7.00–7.60 (m, 17H), 8.05–8.20 (2d, 1H).

後処理

  1. temperatureThe suspension was heated
  2. temperatureunder reflux overnight before the solvent
  3. customwas removed under reduced pressure
  4. extractionThe crude product was extracted (DCM/H2O)
  5. custompurified by flash chromatography (Hex:EtOAc-5:1)

出典と根拠

ORDレコード
ord-9e4f61d2237d45b4808f70a51e5bd1d7
出典データセット
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07192945B2

反応ノート

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