Hydrochloric Acid → N5-(3-acetoxypropyl)-2-amino-N1-n-propylpentane-1,5-diamide hydrochloride

HRID 64935ノート

反応式

HRID 64935 の反応式
[ClH:1].[C:2]([O:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:31])[CH2:11][CH2:12][CH:13]([NH:20]C(OCC1C=CC=CC=1)=O)[C:14]([NH:16][CH2:17][CH2:18][CH3:19])=[O:15])(=[O:4])[CH3:3]>CO.[C].[Pd]>[ClH:1].[C:2]([O:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:31])[CH2:11][CH2:12][CH:13]([NH2:20])[C:14]([NH:16][CH2:17][CH2:18][CH3:19])=[O:15])(=[O:4])[CH3:3]

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 13630459N5-(3-acetoxypropyl)-2-(benzyloxycarbonylamino)-N1-n-propylpentane-1,5-diamide

生成物 1

HCID 86740993N5-(3-acetoxypropyl)-2-amino-N1-n-propylpentane-1,5-diamide hydrochloride

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 887Methanol溶媒

実験手順

In 200 ml of methanol was dissolved 14.6 g of the DL-N5 -(3-acetoxypropyl)-2-(benzyloxycarbonylamino)-N1 -n-propylpentane-1,5-diamide, and thereto were added 1.5 g of 5% palladium-carbon and 8 ml of conc. hydrochloric acid, after which the resulting mixture was subjected to catalytic reduction at room temperature. Subsequently, the palladium-carbon was removed by filtration and the solvent was removed by distillation under reduced pressure to obtain oily DL-N5 -(3-acetoxypropyl)-2-amino-N1 -n-propylpentane-1,5-diamide hydrochloride. This product was dissolved in 50 ml of methylene chloride, and the resulting solution was added dropwise at -20° C. to -10° C. to the mixed acid anhydride in methylene chloride separately prepared in the same manner as in Example 8-(2) from 4.3 g of β-(2-furyl)acrylic acid, 10 ml of triethylamine and 3.7 g of ethyl chlorocarbonate, after which the resulting mixture was stirred at the same temperature for 30 minutes. Subsequently, the mixture was further stirred at room temperature for 30 minutes, and washed successively with 50 ml of diluted hydrochloric acid, 50 ml of a saturated aqueous sodium hydrogencarbonate solution and 50 ml of water, and thereafter dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure to obtain 4.2 g (yield 24%) of DL-N5 -(3-acetoxypropyl)-2-[β-(2-furyl)acrylamido]-N1 -n-propylpentane-1,5-diamide having a melting point of 154°-156° C.

後処理

  1. customwas subjected to catalytic reduction at room temperature
  2. customSubsequently, the palladium-carbon was removed by filtration
  3. customthe solvent was removed by distillation under reduced pressure

出典と根拠

ORDレコード
ord-636d1f4f1c09480e986673c0d081d923
出典データセット
uspto-grants-1986_09
特許番号
US04610983

反応ノート

読み込み中…