2-[1,1-Dimethyl-2-(2-phenylacetamido)ethyl]amino-3',4'-bis(benzyloxy)acetophenone hydrobromide → 2-[1,1-Dimethyl-2-(2-phenylacetamido)ethyl]amino-3',4'-dihydroxyacetophenone hydrobromide

HRID 2417881ノート

反応式

HRID 2417881 の反応式
[BrH:1].[CH3:2][C:3]([NH:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26]CC2C=CC=CC=2)=[C:22]([O:34]CC2C=CC=CC=2)[CH:21]=1)=[O:19])([CH3:15])[CH2:4][NH:5][C:6](=[O:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H][H]>C(O)C.[Pd]>[BrH:1].[CH3:15][C:3]([NH:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([OH:34])[CH:21]=1)=[O:19])([CH3:2])[CH2:4][NH:5][C:6](=[O:14])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

5

反応物 2

HCID 204468152-[1,1-Dimethyl-2-(2-phenylacetamido)ethyl]amino-3',4'-bis(benzyloxy)acetophenone hydrobromideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 204468182-[1,1-Dimethyl-2-(2-phenylacetamido)ethyl]amino-3',4'-dihydroxyacetophenone hydrobromide

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of 2-bromo-3',4'-bis(benzyloxy)acetophenone (5.24 g.) and N-(2-amino-2-methylpropyl)-2-phenylacetamide (5.5 g.) in dioxan (25 ml.) was stirred for 2 hours at room temperature. The reaction mixture was diluted with dry ether (200 ml.) and the precipitate of N-(2-amino-2-methylpropyl)-2-phenylacetamide hydrobromide was separated by filtration. The ethereal filtrate was washed with water (3×50 ml.), brine (100 ml.) dried (MgSO4) and then a fresh solution of saturated ethereal hydrogen bromide was added until the solution was just acid. After 18 hours at 0°-5° C. the precipitate which had formed was collected to give 2-[1,1-dimethyl-2-(2-phenylacetamido)ethyl]amino-3',4'-bis(benzyloxy)acetophenone hydrobromide as a solid (6.85 g.) m.p. 155°-160° C. This hydrobromide (5.0 g.) was dissolved in absolute ethanol (300 ml.) and the solution was hydrognated at atmospheric pressure using 10% w/w palladium-on-carbon (3.0 g.) as catalyst. When the uptake of hydrogen was complete (about 3 hours), the catalyst was removed by filtration and the ethanolic filtrate was evaporated at a temperature below 30° C. to give 2-[1,1-dimethyl-2-(2-phenylacetamido)ethyl]amino-3',4'-dihydroxyacetophenone hydrobromide as a foam (3.7 g.) which was used directly for further acylation.

後処理

  1. custom(about 3 hours)
  2. customthe catalyst was removed by filtration
  3. customthe ethanolic filtrate was evaporated at a temperature below 30° C.

出典と根拠

ORDレコード
ord-3fc64d7e1c9941f18ebeec0fdc1ad071
出典データセット
uspto-grants-1984_09
特許番号
US04470997

反応ノート

読み込み中…