Water → (5R)-3-(6-{4-[3-(Cyclopentylthio)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 2118322ノート

反応式

HRID 2118322 の反応式
[CH3:1][C:2]1([CH3:36])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31](I)[CH:30]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.C(N(CC)CC)C.[CH:44]1([SH:49])[CH2:48][CH2:47][CH2:46][CH2:45]1.O>CN1CCCC1=O.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2].[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[CH:44]1([S:49][C:31]2[CH:30]=[C:29]([CH2:28][CH2:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:14]3[CH2:13][C@@H:12]([C:10]4[CH:9]=[CH:8][C:6]5[O:7][C:2]([CH3:1])([CH3:36])[O:3][CH2:4][C:5]=5[CH:11]=4)[O:16][C:15]3=[O:17])[CH:34]=[CH:33][CH:32]=2)[CH2:48][CH2:47][CH2:46][CH2:45]1

参加物

8

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 15510CyclopentanethiolHCID 69120002(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[4-(3-iodophenyl)butoxy]hexyl}-1,3-oxazolidin-2-one

生成物 1

HCID 69119396(5R)-3-(6-{4-[3-(Cyclopentylthio)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

試薬・触媒・溶媒 3

HCID 9832798Tris(dibenzylideneacetone) dipalladium触媒HCID 152416121,1`-Bis(diphenylphosphino)ferrocene触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
60 °C

実験手順

A stirred solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[4-(3-iodophenyl)butoxy]hexyl}-1,3-oxazolidin-2-one (1.8 g), 1,1 bis(diphenylphosphino) ferrocene (86 mg) and tris(dibenzylideneacetone) di palladium (180 mg) was stirred at room temperature in 1-methyl-2-pyrrolidinone (10 ml) and triethylamine (2 ml) for 10 min under nitrogen. Cyclopentyl mercaptan (0.63 ml) was added and the mixture was heated at 60° C. for 1 h. The mixture was cooled, poured into water and extracted into dichloromethane. The extracts were dried (Na2SO4) and evaporated. The residual oil was purified on a biotage cartridge (90 g) using ether-hexane (3:2) as eluent changing to ether. The appropriate fractions were evaporated to give the title compound (1.07 g).

後処理

  1. temperatureThe mixture was cooled
  2. extractionextracted into dichloromethane
  3. dry with materialThe extracts were dried (Na2SO4)
  4. customevaporated
  5. customThe residual oil was purified on a biotage cartridge (90 g)
  6. customThe appropriate fractions were evaporated

出典と根拠

ORDレコード
ord-51faa41fb1734125b203a2b3e1d5a980
出典データセット
uspto-grants-2008_10
特許番号
US07442839B2

反応ノート

読み込み中…