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Potassium Carbonate → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(2-isopropenyl-1,3-thiazol-4-yl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

HRID 1994557
ノート
印刷プレビュー

反応式

HRID 1994557 の反応式
Br[C:2]1[N:3]=[C:4]([C:7]([CH3:9])=[CH2:8])[S:5][CH:6]=1.[F:10][C:11]([F:50])([F:49])[C:12]1[CH:13]=[C:14]([C@H:22]2[O:26][C:25](=[O:27])[N:24]([CH2:28][C:29]3[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][C:30]=3B3OC(C)(C)C(C)(C)O3)[C@H:23]2[CH3:48])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[F:50][C:11]([F:10])([F:49])[C:12]1[CH:13]=[C:14]([C@H:22]2[O:26][C:25](=[O:27])[N:24]([CH2:28][C:29]3[CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=[CH:31][C:30]=3[C:2]3[N:3]=[C:4]([C:7]([CH3:9])=[CH2:8])[S:5][CH:6]=3)[C@H:23]2[CH3:48])[CH:15]=[C:16]([C:18]([F:19])([F:21])[F:20])[CH:17]=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 11430Potassium CarbonateHCID 112294714-Bromo-2-isopropenyl-1,3-thiazoleHCID 57704783(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one

生成物 1

HCID 11505288(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(2-isopropenyl-1,3-thiazol-4-yl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

In a tube were placed 4-bromo-2-isopropenyl-1,3-thiazole (20 mg, 0.097 mmol), (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one (29.4 mg, 0.0492 mmol), THF (340 μL), 1M aqueous K2CO3 (340 μL), and 1,1-bis(di-t-butylphosphino)ferrocene palladium chloride (3.2 mg, 4.9×10−3 mmol). The mixture was degassed with N2. The tube was sealed and heated at 100° C. for 1.5 hours. The reaction was then cooled to room temperature, diluted with EtOAc (50 mL), and washed with water and brine (15 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (5 to 25% EtOAc/hexanes) and then by PTLC (90% CH2Cl2/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(2-isopropenyl-1,3-thiazol-4-yl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one. Rf=0.16 (15% EtOAc/hexanes). LCMS=595.1 (M+1)+. 1H NMR (CD2Cl2, 500 MHz) δ 7.90 (s, 1H), 7.64-7.76 (m, 5H), 7.38 (s, 1H), 5.89 (s, 1H), 5.60 (d, J=8.1 Hz, 1H), 5.37 (d, J=1.2 Hz, 1H), 4.99 (d, J=16.0 Hz, 1H), 4.66 (d, J=16.0 Hz, 1H), 3.94 (m, 1H), 2.25 (s, 3H), 0.59 (d, J=6.4 Hz, 3H).

後処理

  1. customIn a tube were placed
  2. customThe mixture was degassed with N2
  3. customThe tube was sealed
  4. temperatureThe reaction was then cooled to room temperature
  5. additiondiluted with EtOAc (50 mL)
  6. washwashed with water and brine (15 mL each)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the residue by flash chromatography on silica gel (5 to 25% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-8d04e5648b034ffcb1c3b804675e8338
出典データセット
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07652049B2

反応ノート

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