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1,4-Dioxane → (R)-4-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)-4-methyloxazolidin-2-one

HRID 1036451
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HRID 1036451 반응식
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C@:17]3([CH3:23])[CH2:21][O:20][C:19](=[O:22])[NH:18]3)[CH:13]=2)[CH:8]=1)(=O)=O.[CH2:26]([O:33][C:34]1[CH:35]=[C:36]([SH:40])[CH:37]=[CH:38][CH:39]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.O1CCOCC1.C(N(CC)C(C)C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:26]([O:33][C:34]1[CH:35]=[C:36]([S:40][C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[C:12]([C@:17]2([CH3:23])[CH2:21][O:20][C:19](=[O:22])[NH:18]2)[CH:11]=[CH:10]3)[CH:37]=[CH:38][CH:39]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1
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참가 물질

7

반응물 5

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 249006013-(Benzyloxy)benzene-1-thiolHCID 86642894(R)-6-(4-methyl-2-oxooxazolidin-4-yl)naphthalen-2-yl trifluoromethanesulfonate

생성물 1

HCID 67413241
(R)-4-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)-4-methyloxazolidin-2-one

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

실험 절차

(R)-6-(4-methyl-2-oxooxazolidin-4-yl)naphthalen-2-yl trifluoromethanesulfonate (30.0 mg, 0.0000799 mol), 3-benzyloxy-benzenethiol (20.7 mg, 0.0000959 mol), tris(dibenzylideneacetone)dipalladium(0) (8.78 mg, 9.59E-6 mol) and xantphos (11.1 mg, 0.0000192 mol) were dissolved in 1,4-dioxane (3 mL, 0.04 mol, anhydrous), degassed in low vacuum and backfilled with N2 five times. N,N-diisopropylethylamine (0.0418 mL, 0.000240 mol) pre-degassed in the same way was added under N2 atomsphere. The mixture was heated to reflux for 20 hours. The mixture was cooled to room temperature, filtered, evaporated, and the residue was chromatographed with EtOAc/hexane (0:100 to 10:90) to give (R)-4-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)-4-methyloxazolidin-2-one as a solid product (30.0 mg, 85%). Rf (EtOAc:hexane=1:9)=0.3.

후처리

  1. customdegassed in low vacuum
  2. additionwas added under N2 atomsphere
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 20 hours
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was chromatographed with EtOAc/hexane (0:100 to 10:90)

출처 및 근거

ORD 기록
ord-e5128d288b344999b9e239f72c930a94
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546359B2

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