Isopropanol → (2S)-2-(1-Adamantylmethoxycarbonylamino)-3-((5-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-thiophene-2-carbonyl)-amino)-propionic Acid Isopropyl Ester

HRID 413222노트

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HRID 413222 반응식
[C:1]12([CH2:11][O:12][C:13]([NH:15][C@@H:16]([CH2:20][NH:21][C:22]([C:24]3[S:25][C:26]([CH2:29][CH2:30][C:31](=[O:39])[NH:32][C:33]4[NH:34][CH2:35][CH2:36][CH2:37][N:38]=4)=[CH:27][CH:28]=3)=[O:23])[C:17]([OH:19])=[O:18])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(Cl)(Cl)=O.[CH:44](O)([CH3:46])[CH3:45]>>[CH:44]([O:18][C:17](=[O:19])[C@@H:16]([NH:15][C:13]([O:12][CH2:11][C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2)=[O:14])[CH2:20][NH:21][C:22]([C:24]1[S:25][C:26]([CH2:29][CH2:30][C:31](=[O:39])[NH:32][C:33]2[NH:34][CH2:35][CH2:36][CH2:37][N:38]=2)=[CH:27][CH:28]=1)=[O:23])([CH3:46])[CH3:45]

참가 물질

4

반응물 3

HCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 10415384(S)-2-(Adamantan-1-ylmethoxycarbonylamino)-3-{[5-(3-guanidino-3-oxo-propyl)-thiophene-2-carbonyl]-amino}-propionic acid

생성물 1

HCID 15859416(2S)-2-(1-Adamantylmethoxycarbonylamino)-3-((5-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-thiophene-2-carbonyl)-amino)-propionic Acid Isopropyl Ester

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온도
50 °C

실험 절차

0.559 g (1 mmol) of (2S)-2-(1-adamantylmethoxycarbonylamino)-3-((5-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-thiophene-2-carbonyl)-amino)-propionic acid (example 15) were dissolved in 10 ml of isopropanol. Under an inert gas atmosphere and under external cooling 0.26 ml of thionyl chloride were cautiously added. After stirring for 8 hours at 50° C. the reaction was complete. The solvents were removed in vacuo to give a colourless foam which was purified by chromatography (silica gel; isopropanol/ethyl acetate/water (4/3/1; v/v/v)). The fractions containing the title compound were lyopholized to give 0.27 g of a colourless fluffy material.

후처리

  1. additionwere cautiously added
  2. customThe solvents were removed in vacuo
  3. customto give a colourless foam which
  4. customwas purified by chromatography (silica gel; isopropanol/ethyl acetate/water (4/3/1; v/v/v))
  5. additionThe fractions containing the title compound

출처 및 근거

ORD 기록
ord-c10c4fbf30dc4b2b9f8d06496f9e7724
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566366B1

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