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Ethyl Acetate → HCID 57389225、化合物

HRID 1184733
ノート
印刷プレビュー

反応式

HRID 1184733 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([OH:33])[CH2:15][C:16]2[C:21](Cl)=[CH:20][N:19]=[C:18]([C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[O:33][C:21]3[CH:20]=[N:19][C:18]([C:23]4[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=4)=[N:17][C:16]=3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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

7

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 67973476HCID 67973476、化合物

生成物 1

HCID 57389225HCID 57389225、化合物

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate
触媒
HCID 1140Toluene溶媒

反応条件

温度
70 °C

実験手順

A mixture of 4-{2-[5-chloro-2-(4-methanesulfonyl-phenyl)-pyrimidin-4-yl]-1-hydroxy-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (50 mg), palladium acetate (3 mg), racemic 2-(di-tert-butylphosphino)-1,1′-binapthyl (6 mg), and cesium carbonate (50 mg) in toluene (1 mL) is heated in an oil bath at 70° C. under an argon atmosphere for 6 h. After cooling to room temperature ethyl acetate is added and the organic phase is separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel [dichloromethane/(dichloromethane/methanol/NH4OH 24:24:1) 96:4→90:10]. The crude product is triturated with diethyl ether, filtered off, and dried to give the title compound. LC (method 7): tR=1.44 min; Mass spectrum (ESI+): m/z=460 [M+H]+.

後処理

  1. additionis added
  2. customthe organic phase is separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on silica gel [dichloromethane/(dichloromethane/methanol/NH4OH 24:24:1) 96:4→90:10]
  7. customThe crude product is triturated with diethyl ether
  8. filtrationfiltered off
  9. customdried

出典と根拠

ORDレコード
ord-c05aaccbb9aa478ba44e1cc039664951
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08669271B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート