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 2118322노트

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HRID 2118322 반응식
[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

참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 3

HCID 9832798Tris(dibenzylideneacetone) dipalladium촉매HCID 152416121,1`-Bis(diphenylphosphino)ferrocene촉매HCID 13387N-methyl-2-pyrrolidone용매

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온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-51faa41fb1734125b203a2b3e1d5a980
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442839B2

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