Triethylamine → 3-t-Butoxycarbonyl-4(R)-[3-(4-diphenylmethyl-1-piperazinyl)propylcarbamoyl]-2-(3-pyridyl)thiazolidine

HRID 129748

反応式

HRID 129748 の反応式
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]([OH:15])=O)[CH2:11][S:10][CH:9]1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([CH:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:28][CH2:27]1.C(P(C#N)(CC)=O)C.C(N(CC)CC)C>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13](=[O:15])[NH:22][CH2:23][CH2:24][CH2:25][N:26]2[CH2:27][CH2:28][N:29]([CH:32]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:30][CH2:31]2)[CH2:11][S:10][CH:9]1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 100867263-t-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4(R)-carboxylic acidHCID 13586794DiethylphosphorylcyanideHCID 137677783-(4-Benzhydryl-1-piperazinyl)-1-propanamine

生成物 1

HCID 228575693-t-Butoxycarbonyl-4(R)-[3-(4-diphenylmethyl-1-piperazinyl)propylcarbamoyl]-2-(3-pyridyl)thiazolidine収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 500 mg (1.61 mmole) of 3-t-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4(R)-carboxylic acid, 500 mg (1.61 mmole) of 1-(3-aminopropyl)-4-(diphenylmethyl) piperazine (prepared as described in Preparation 16'), 263 mg (1.61 mmole) of diethylphosphoryl cyanide, 163 mg (1.61 mmole) of triethylamine and 10 ml of tetrahydrofuran was stirred at room temperature overnight. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, diluted with water and extracted with methylene chloride. The solvent was then removed by evaporation under reduced pressure, and the resulting residue was subjected to column chromatography through alumina, using ethyl acetate as the eluent, to afford 840 mg (yield 89%) of the title compound as an oil.

後処理

  1. customprepared
  2. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  3. additiondiluted with water
  4. extractionextracted with methylene chloride
  5. customThe solvent was then removed by evaporation under reduced pressure

出典と根拠

ORDレコード
ord-a518341421784649ae78ee248a1bc59d
出典データセット
uspto-grants-1995_11
特許番号
US05470851

関連ノート

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