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Tris(furan-2-yl)phosphane → N-{[(5S)-3-(4-{2-[5-(Hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyrid-5-yl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide

HRID 747254
ノート
印刷プレビュー

反応式

HRID 747254 の反応式
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Sn](C)(C)C)=[CH:9][CH:8]=2)[CH2:5][C@H:4]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:3]1.Br[C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH2:33][CH:32]([CH2:34][OH:35])[O:31][N:30]=2)=[N:27][CH:28]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[OH:35][CH2:34][CH:32]1[O:31][N:30]=[C:29]([C:26]2[CH:25]=[CH:24][C:23]([C:10]3[CH:11]=[CH:12][C:7]([N:6]4[CH2:5][C@H:4]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:3][C:2]4=[O:1])=[CH:8][CH:9]=3)=[CH:28][N:27]=2)[CH2:33]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 14987823N-({(5S)-2-Oxo-3-[4-(trimethylstannyl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamideHCID 17954471[3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

生成物 1

HCID 59749496N-{[(5S)-3-(4-{2-[5-(Hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyrid-5-yl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide収率 26.8%

試薬・触媒・溶媒 1

HCID 11029508
Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)
触媒

反応条件

温度
90 °C

実験手順

N-({(5S)-2-Oxo-3-[4-(trimethylstannyl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide (300 mg, 0.76 mM), [3-(5-bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methanol (194 mg, 0.76 mM), tris(dibenzylideneacetone)dipalladium (0)-chloroform adduct (78 mg, 0.076 mM) and tri-2-furylphosphine (35 mg, 0.152 mM) were placed in a flask. The solids were degassed and placed under nitrogen. Anhydrous dioxane (5 ml) was added and the suspension was heated at 90° C. for 15 hours. The reaction mixture was cooled and the solvent was evaporated. The residue was chromatographed on silica gel eluting with 5% methanol in dichloromethane to give the title compound (83 mg).

後処理

  1. customThe solids were degassed
  2. additionAnhydrous dioxane (5 ml) was added
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was evaporated
  5. customThe residue was chromatographed on silica gel eluting with 5% methanol in dichloromethane

出典と根拠

ORDレコード
ord-91e2c70c93714856a09bf6ac106d05ea
出典データセット
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07396847B2

反応ノート

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