Potassium Phosphate, Tribasic → (2R,3R,4R,5S,6S)-2-(Acetoxymethyl)-6-(5-(4-ethylbenzyl)-4'-methoxy-6-methylbiphenyl-3-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

HRID 576370ノート

反応式

HRID 576370 の反応式
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[C:23]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH3:33])=[CH:28][CH:27]=3)[C:22]([CH3:34])=[C:21](Br)[CH:20]=2)[O:7][C@@H:6]1[CH2:36][O:37][C:38](=[O:40])[CH3:39])(=[O:3])[CH3:2].[CH3:41][O:42][C:43]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45][CH:44]=1.F[B-](F)(F)F.C1([PH+](C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:20]=[C:21]([C:46]3[CH:47]=[CH:48][C:43]([O:42][CH3:41])=[CH:44][CH:45]=3)[C:22]([CH3:34])=[C:23]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH3:33])=[CH:28][CH:27]=3)[CH:24]=2)[O:7][C@@H:6]1[CH2:36][O:37][C:38](=[O:40])[CH3:39])(=[O:3])[CH3:2]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 201262(4-Methoxyphenyl)boronic acidHCID 11710396Tricyclohexylphosphonium TetrafluoroborateHCID 59238239(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylphenyl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

生成物 1

HCID 71110869(2R,3R,4R,5S,6S)-2-(Acetoxymethyl)-6-(5-(4-ethylbenzyl)-4'-methoxy-6-methylbiphenyl-3-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate収率 93%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylphenyl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate (131) (WO2008/101939, Example V) (500 mg, 0.807 mmole) in toluene (6 mL) and water (3 mL) were added 4-methoxyphenylboronic acid (147 mg, 0.969 mmole), Pd(OAc)2 (18.1 mg, 0.0807 mmole), tricyclohexylphosphonium tetrafluoroborate (59.4 mg, 0.161 mmole), and K3PO4 (685 mg, 3.23 mmole). The mixture was stirred at 100° C. overnight. After cooling to ambient temperature, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel chromatography to yield the title compound (484 mg, 0.748 mmole, 93%) as a yellow solid.

後処理

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-6325ddb9c28d473789558e40d1f8e30a
出典データセット
uspto-grants-2015_05
特許番号
US09034921B2

反応ノート

読み込み中…