Bis(2-chloroethyl)ethylamine → methyl (S)-3-tert-butoxycarbonylamino-2-(4-ethylpiperazin-1-yl)propanoate

HRID 472139

反応式

HRID 472139 の反応式
Cl.[NH2:2][C@@H:3]([CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:4]([O:6][CH3:7])=[O:5].Cl[CH2:18][CH2:19][N:20]([CH2:23][CH2:24]Cl)[CH2:21][CH3:22]>C(N(CC)C(C)C)(C)C>[C:13]([O:12][C:10]([NH:9][CH2:8][C@H:3]([N:2]1[CH2:22][CH2:21][N:20]([CH2:23][CH3:24])[CH2:19][CH2:18]1)[C:4]([O:6][CH3:7])=[O:5])=[O:11])([CH3:16])([CH3:15])[CH3:14]

参加物

4

反応物 2

HCID 10848Bis(2-chloroethyl)ethylamineHCID 18334328methyl (2S)-2-amino-3-{[(tert-butoxy)carbonyl]amino}propanoate hydrochloride

生成物 1

HCID 86667916methyl (S)-3-tert-butoxycarbonylamino-2-(4-ethylpiperazin-1-yl)propanoate収率 40.4%

試薬・触媒・溶媒 1

HCID 81531Diisopropylethylamine溶媒

実験手順

A solution of 5.0 g (19.6 mmol) of commercial methyl (S)-2-amino-3-tert-butoxycarbonylaminopropanoate hydrochloride and 3.3 g (19.6 mmol) of bis(2-chloroethyl)ethylamine in 50 ml of N,N-diisopropylethylamine is heated at 127° C. for 5 h. After evaporation of a maximum amount of diisopropylethylamine, the reaction medium is diluted with ethyl acetate and washed with an aqueous solution of sodium hydroxide having a concentration of 1N. The organic phase obtained is then washed with water, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude product obtained is purified by chromatography on silica gel, elution being carried out with a 30/70 heptane/ethyl acetate mixture. 2.5 g (40%) of methyl (S)-3-tert-butoxycarbonylamino-2-(4-ethylpiperazin-1-yl)propanoate are obtained in the form of an oil.

後処理

  1. customAfter evaporation of a maximum amount of diisopropylethylamine
  2. additionthe reaction medium is diluted with ethyl acetate
  3. washwashed with an aqueous solution of sodium hydroxide having a concentration of 1N
  4. customThe organic phase obtained
  5. washis then washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude product obtained
  10. customis purified by chromatography on silica gel, elution

出典と根拠

ORDレコード
ord-5b8276e7ad04491eab2dda887c0b0d7f
出典データセット
uspto-grants-2014_01
特許番号
US08633196B2

関連ノート

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