Tris(furan-2-yl)phosphane → (5R)-3-{4'-[5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

HRID 747235

反応式

HRID 747235 の反応式
[Si:1]([O:8][CH2:9][CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([Sn](C)(C)C)=[CH:17][CH:16]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:36][C@H:35]([CH2:37][N:38]3[CH:42]=[C:41]([CH3:43])[N:40]=[N:39]3)[O:34][C:33]2=[O:44])=[CH:28][CH:27]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>O1CCOCC1.[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>[Si:1]([O:8][CH2:9][CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH2:36][C@H:35]([CH2:37][N:38]5[CH:42]=[C:41]([CH3:43])[N:40]=[N:39]5)[O:34][C:33]4=[O:44])=[CH:28][CH:27]=3)=[CH:17][CH:16]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 597494295-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-3-[4-(trimethylstannyl)phenyl]4,5-dihydroisoxazoleHCID 59749434(5R)-3-(4-Iodophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

生成物 1

HCID 59749445(5R)-3-{4'-[5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one収率 28.3%

試薬・触媒・溶媒 2

HCID 44556509Tris(dibenzylideneacetone) palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

5-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-3-[4-(trimethylstannyl)phenyl]4,5-dihydroisoxazole (0.70 g, 1.6 mmol), (5R)-3-(4-iodophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (0.5 g, 1.29 mmol), tri-2-furyl phosphine (0.06 g, 0.26 mmol) and tris(dibenzylideneacetone)palladium (0) (0.12 g, 0.13 mmol) were dissolved in 1,4-dioxane (5 ml) and degassed three times. The mixture was then heated to 90° C. and stirred for 18 hr. LCMS indicated that the reaction was not yet complete, so it was cooled and an additional (0.12 g, 0.13 mmol) of tris(dibenzylidene acetone) palladium (0) was added, the mixture degassed and reheated to 110° C. for 3 hours, and 25° C. for 40 hours. The solution was concentrated in vacuo and purified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent giving 0.2 g of the desired product as a yellow solid.

後処理

  1. customdegassed three times
  2. temperatureso it was cooled
  3. customthe mixture degassed
  4. waitreheated to 110° C. for 3 hours
  5. wait25° C. for 40 hours
  6. concentrationThe solution was concentrated in vacuo
  7. custompurified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent

出典と根拠

ORDレコード
ord-aa766d7d8b7b4900aa80758113d2bce9
出典データセット
uspto-grants-2008_07
特許番号
US07396847B2

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