3(R)-amino-2,3-dihydro-1,5(5H)-benzothiazepin-4-one → 3(R)-[5-(1-benzyloxycarbonyl-4-piperidyl)-1-ethoxycarbonylpentyl]amino-2,3-dihydro-1,5(5H)-benzothiazepin-4-one

HRID 649413ノート

反応式

HRID 649413 の反応式
[NH2:1][C@@H:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[S:4][CH2:3]1.[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH:34](OS(C)(=O)=O)[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:26][CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OC(=O)C)C>[CH2:14]([O:21][C:22]([N:24]1[CH2:25][CH2:26][CH:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH:34]([NH:1][C@@H:2]2[C:8](=[O:9])[NH:7][C:6]3[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=3[S:4][CH2:3]2)[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:28][CH2:29]1)=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

4

反応物 2

HCID 133751443(R)-amino-2,3-dihydro-1,5(5H)-benzothiazepin-4-oneHCID 13652732Ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-methanesulfonyloxyhexanoate

生成物 1

HCID 704162703(R)-[5-(1-benzyloxycarbonyl-4-piperidyl)-1-ethoxycarbonylpentyl]amino-2,3-dihydro-1,5(5H)-benzothiazepin-4-one収率 44.2%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3(R)-amino-2,3-dihydro-1,5(5H)-benzothiazepin-4-one (2.7 g) and ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-methanesulfonyloxyhexanoate (5.4 g) is heated at 100°-130° C. for 3 hours. After cooling, the mixture is dissolved in ethylacetate (200 ml) and the solution is washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 3(R)-[5-(1-benzyloxycarbonyl-4-piperidyl)-1-ethoxycarbonylpentyl]amino-2,3-dihydro-1,5(5H)-benzothiazepin-4-one (2.9 g) as a colorless oil.

後処理

  1. temperatureis heated at 100°-130° C. for 3 hours
  2. temperatureAfter cooling
  3. washthe solution is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-b3edba3aa446461aa2ce3ac5196558a6
出典データセット
uspto-grants-1988_04
特許番号
US04739066

反応ノート

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