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

HRID 129748Notes

Reaction equation

HRID 129748 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a518341421784649ae78ee248a1bc59d
Source dataset
uspto-grants-1995_11
Patent number
US05470851

Reaction notes

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