Water → HCID 86629751、化合物

HRID 1510233ノート

反応式

HRID 1510233 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[CH:10]([OH:18])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].O>ClCCl.O1CCCC1.CN(C)C1C=CN=CC=1>[CH3:29][S:30]([O:18][CH:10]([CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:19])(=[O:32])=[O:31]

参加物

8

反応物 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69080060HCID 69080060、化合物

生成物 1

HCID 86629751HCID 86629751、化合物

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-(4-bromophenyl)-2-hydroxy-3-phenylpropanamide (1.5 g) in dichloromethane (60 mL) and tetrahydrofuran (30 mL) were added diisopropylethylamine (908 mg) and 4-dimethylaminopyridine (114 mg), followed by dropwise addition of methanesulfonyl chloride (805 mg) at 5° C. and the mixture was stirred at ambient temperature for 20 hours. The mixture was poured into water and concentrated in vacuo. The residue was extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, and evaporated in vacuo to afford crude 1-benzyl-2-[(4-bromophenyl)amino]-2-oxoethyl methanesulfonate. The crude methanesulfonate was dissolved in N,N-dimethylformamide (30 mL) and 4-piperidinol (1.19 g) was added. The mixture was stirred at 80° C. for 5 hours and poured into water. The mixture was extracted with ethyl acetate, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to afford N-(4-bromophenyl)-2-(4-hydroxypiperidin-1-yl)-3-phenylpropanamide (894 mg) as a powder.

後処理

  1. concentrationconcentrated in vacuo
  2. extractionThe residue was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-2f805dfa806748dba85eedd7d6980928
出典データセット
uspto-grants-2012_07
特許番号
US08211919B2

反応ノート

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