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

HRID 1036451
ノート
印刷プレビュー

反応式

HRID 1036451 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-e5128d288b344999b9e239f72c930a94
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546359B2

反応ノート

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