Sodium hydride → (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[4-(3-iodophenyl)butoxy]hexyl}-1,3-oxazolidin-2-one

HRID 2118321ノート

反応式

HRID 2118321 の反応式
[H-].[Na+].[CH3:3][C:4]1([CH3:20])[O:9][C:8]2[CH:10]=[CH:11][C:12]([C@H:14]3[O:18][C:17](=[O:19])[NH:16][CH2:15]3)=[CH:13][C:7]=2[CH2:6][O:5]1.[I:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]Br)[CH:25]=[CH:26][CH:27]=1.[Cl-].[NH4+]>CN(C=O)C>[CH3:3][C:4]1([CH3:20])[O:9][C:8]2[CH:10]=[CH:11][C:12]([C@H:14]3[O:18][C:17](=[O:19])[N:16]([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][O:32][CH2:31][CH2:30][CH2:29][CH2:28][C:24]4[CH:25]=[CH:26][CH:27]=[C:22]([I:21])[CH:23]=4)[CH2:15]3)=[CH:13][C:7]=2[CH2:6][O:5]1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneHCID 691198836-Bromohexyl 4-(3-iodophenyl)butyl ether

生成物 1

HCID 69120002(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[4-(3-iodophenyl)butoxy]hexyl}-1,3-oxazolidin-2-one収率 73.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
50 °C

実験手順

Sodium hydride (60% dispersion in oil 1.26 g) was added to a stirred, cooled (ice-bath) solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxazolidinone (5.47 g) in dry DMF (50 ml) under nitrogen and the mixture was stirred for 15 min at 50° C. A solution of 6-bromohexyl 4-(3-iodophenyl)butyl ether (10.7 g) in DMF (30 ml) was then added dropwise over 10 min. The mixture was stirred for 2 h at ambient temperature, then poured into aqueous solution of ammonium chloride and extracted into ethyl acetate. The combined extracts were washed with water, dried (Na2SO4) and evaporated. The residue was purified on biotage (90 g cartridge) eluting with ether-hexane (3:2) to give the title compound (9.8 g). LCMS RT=4.20 min.

後処理

  1. stirringThe mixture was stirred for 2 h at ambient temperature
  2. extractionextracted into ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified on biotage (90 g cartridge)
  7. washeluting with ether-hexane (3:2)

出典と根拠

ORDレコード
ord-de1f4bb28dc541d7baf2ede4bb30bacc
出典データセット
uspto-grants-2008_10
特許番号
US07442839B2

反応ノート

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