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Urea → N-[2-(4-Carbomethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(4-methyl-oxazol-5-yl)ethanamine dihydrochloride

HRID 1451413
ノート
印刷プレビュー

反応式

HRID 1451413 の反応式
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7](=[O:10])[CH2:8]Br.C(N(CC)C(C)C)(C)C.[C:20]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH:31]([NH2:33])[CH3:32])=[CH:26][CH:25]=1)([O:22][CH3:23])=[O:21].NC(N)=O.[BH4-].[Na+].C(Cl)[Cl:41]>CO>[ClH:41].[ClH:41].[C:20]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH:31]([NH:33][CH2:8][CH:7]([OH:10])[C:6]2[O:5][CH:4]=[N:3][C:2]=2[CH3:1])[CH3:32])=[CH:26][CH:25]=1)([O:22][CH3:23])=[O:21]
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

8

反応物 6

HCID 1176UreaHCID 6344Dichloromethane2 回HCID 81531DiisopropylethylamineHCID 4311764Sodium borohydrideHCID 15034329Methyl 4-(2-aminopropyl)benzoateHCID 199743052-Bromo-1-(4-methyloxazol-5-yl)ethanone

生成物 1

HCID 14076231
N-[2-(4-Carbomethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(4-methyl-oxazol-5-yl)ethanamine dihydrochloride

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
35 °C

実験手順

2.6 g (0.009 mol) of 4-Methyl-5-bromoacetyl-oxazole and 1.16 g (0.009 mol) of N,N-diisopropyl-ethylamine are dissolved in 50 ml of methylene chloride. This solution is added dropwise, within 20 minutes to 3.47 g (0.018 mol) of 2-(4-carbomethoxyphenyl)-1-methylethylamine in 100 ml of methylene chloride, and the mixture is stirred at room temperature for 2 hours and at 35° C. for 1 hour. The reaction solution is cooled in an ice bath, and 150 ml of methanol are added. Then, for the reduction of the resulting amino-ketone, 1 g of sodium borohydride is added in portions over 30 minutes, and the mixture is stirred at room temperature for 20 hours and then evaporated. Ice-water is then added to the residue, and the mixture is acidified with hydrochloric acid, made alkaline with concentrated aqueous ammonia and extracted with chloroform. The extract is dried over sodium sulphate, concentrated and purified on a silica gel column using ethyl acetate/methanol=9:1 as eluant. The hydrochloride is then precipitated with ethereal hydrochloric acid.

後処理

  1. temperatureThe reaction solution is cooled in an ice bath
  2. stirringthe mixture is stirred at room temperature for 20 hours
  3. customevaporated
  4. additionIce-water is then added to the residue
  5. extractionextracted with chloroform
  6. dry with materialThe extract is dried over sodium sulphate
  7. concentrationconcentrated
  8. custompurified on a silica gel column
  9. customThe hydrochloride is then precipitated with ethereal hydrochloric acid

出典と根拠

ORDレコード
ord-a4424c628b90477b9dd25b5dedc648d7
出典データセット
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05604225

反応ノート

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