(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one → (5R)-3-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 219051ノート

反応式

HRID 219051 の反応式
CC(C)([O-])C.[K+].[CH3:7][C:8]1([CH3:24])[O:13][C:12]2[CH:14]=[CH:15][C:16]([C@H:18]3[O:22][C:21](=[O:23])[NH:20][CH2:19]3)=[CH:17][C:11]=2[CH2:10][O:9]1.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][C:37]1[C:42]([Cl:43])=[CH:41][CH:40]=[CH:39][C:38]=1[Cl:44]>CN(C=O)C>[Cl:43][C:42]1[CH:41]=[CH:40][CH:39]=[C:38]([Cl:44])[C:37]=1[CH2:36][O:35][CH2:34][CH2:33][O:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][N:20]1[CH2:19][C@@H:18]([C:16]2[CH:15]=[CH:14][C:12]3[O:13][C:8]([CH3:24])([CH3:7])[O:9][CH2:10][C:11]=3[CH:17]=2)[O:22][C:21]1=[O:23]

参加物

5

反応物 3

HCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneHCID 23665647Potassium tert-butoxideHCID 668449032-((2-((6-Bromohexyl)oxy)ethoxy)methyl)-1,3-dichlorobenzene

生成物 1

HCID 46833391(5R)-3-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one収率 100.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Potassium tert-butoxide (4.38 g, 39 mmol) was added to a solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (9.3 g, 39 mmol) in anhydrous DMF (100 mL) under N2 and the reaction stirred for 1 h at ambient temperature. A solution of 2-[2-(6-bromo-hexyloxy)-ethoxymethyl]-1,3-dichloro-benzene (15 g, 39 mmol) in anhydrous DMF (25 mL) was added and the reaction allowed to stir at ambient temperature for 20 h. The reaction mixture was poured into ice/water (350 mL) and extracted with ethyl acetate (300 mL). The organic layer was separated then washed successively with water/saturated brine (250 mL/25 mL), water/brine (25 mL/10 mL) and finally brine (150 mL), before drying over sodium sulfate. The solution was concentrated to dryness under vacuum to afford the title compound as an oil (21.6 g)—LC RT=6.8 min.

後処理

  1. stirringto stir at ambient temperature for 20 h
  2. extractionextracted with ethyl acetate (300 mL)
  3. customThe organic layer was separated
  4. washthen washed successively with water/saturated brine (250 mL/25 mL), water/brine (25 mL/10 mL) and finally brine (150 mL)
  5. dry with materialbefore drying over sodium sulfate
  6. concentrationThe solution was concentrated to dryness under vacuum

出典と根拠

ORDレコード
ord-69c7ad375c584683bb80a9d69aeccebb
出典データセット
uspto-grants-2012_06
特許番号
US08198483B2

反応ノート

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