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

HRID 747245ノート

反応式

HRID 747245 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[S:27][C:26]([C:28]2[CH2:32][CH:31]([CH2:33][OH:34])[O:30][N:29]=2)=[CH:25][CH:24]=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:34][CH2:33][CH:31]1[O:30][N:29]=[C:28]([C:26]2[S:27][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:24][CH:25]=2)[CH2:32]1

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 17954475[3-(5-Bromothien-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

生成物 1

HCID 59749493N-{[(5S)-3-(4-{5-[5-(Hydroxymethyl)-4,5-dihydroisoxazol-3-yl]thien-2-yl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide収率 42.1%

試薬・触媒・溶媒 1

HCID 11029508Palladium, 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 (500 mg, 1.26 mM), [3-(5-bromothien-2-yl)-4,5-dihydroisoxazol-5-yl]methanol (330 mg, 1.26 mM), tris(dibenzylideneacetone)dipalladium (0)-chloroform adduct (130 mg, 0.126 mM) and tri-2-furylphosphine (58 mg, 0.252 mM) were placed in a flask. The solids were degassed and placed under nitrogen. Anhydrous dioxane (10 ml) was added and the suspension was heated at 90° C. for 16 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 (220 mg).

後処理

  1. customThe solids were degassed
  2. additionAnhydrous dioxane (10 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-024e81dc726548a48e69f0ca86a3a623
出典データセット
uspto-grants-2008_07
特許番号
US07396847B2

反応ノート

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