tert-butyl 3(RS)-[5-(1-benzyloxycarbonyl-4-piperidyl)-1(RS)-ethoxycarbonylpentyl]amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetate → 3(RS)-[5-(4-piperidinyl)-1(RS)-ethoxycarbonylpentyl]amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetic acid.hydrobromide

HRID 2351229ノート

反応式

HRID 2351229 の反応式
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([NH:27][CH:28]2[CH2:34][CH2:33][C:32]3[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=3[N:30]([CH2:39][C:40]([O:42]C(C)(C)C)=[O:41])[C:29]2=[O:47])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[BrH:48].C(O)(=O)C>C(O)(=O)C.C(OCC)C>[NH:11]1[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([NH:27][CH:28]2[CH2:34][CH2:33][C:32]3[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=3[N:30]([CH2:39][C:40]([OH:42])=[O:41])[C:29]2=[O:47])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:15][CH2:16]1.[BrH:48]

参加物

5

反応物 2

HCID 14407252tert-butyl 3(RS)-[5-(1-benzyloxycarbonyl-4-piperidyl)-1(RS)-ethoxycarbonylpentyl]amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetateHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

生成物 1

HCID 221684123(RS)-[5-(4-piperidinyl)-1(RS)-ethoxycarbonylpentyl]amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetic acid.hydrobromide

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 3283Diethyl Ether溶媒

実験手順

In 2 ml of acetic acid is dissolved 0.8 g of tert-butyl 3(RS)-[5-(1-benzyloxycarbonyl-4-piperidyl)-1(SR)-ethoxycarbonylpentyl]amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetate, and 2 ml of 30% aqueous hydrogen bromide-acetic acid solution is added to the solution, followed by standing at room temperature for 2 hours. The reaction solution is diluted with 200 ml of ethyl ether, and after the mixture is allowed to stand, the supernatant layer is removed by decantation. The precipitate is rinsed with 100 ml of ethyl ether and dried to give 3(RS)-[5-(4-piperidyl)-1(SR)-ethoxycarbonylpentyl]amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetic acid·hydrobromide. This product is dissolved in 20 ml of 1N aqueous sodium hydroxide and the solution is allowed to stand at room temperature for 1 hour, acidified with 2 ml of acetic acid and purified by XAD-2 column chromatography (methanol:water=1:1). The effluent is concentrated under reduced pressure, and the crystals, which separate out, are rinsed with 50 ml of acetone and collected by filtration to give 0.33 g of 3(RS)-[5-(4-piperidyl)-1(SR)-carboxypentyl]amino-2-oxo-2,3,4,5-tetrahydro-1H-benzazepine-1-acetic acid as colorless prisms. m.p. 250°-260° C. (decomp.).

後処理

  1. additionis added to the solution
  2. customthe supernatant layer is removed by decantation
  3. washThe precipitate is rinsed with 100 ml of ethyl ether
  4. customdried

出典と根拠

ORDレコード
ord-bea909de254a4294942f483235df3dc6
出典データセット
uspto-grants-1989_10
特許番号
US04871842

反応ノート

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