Triethylamine → N-[{1-(2-chlorophenyl)methyl-2-propylthio-1H-imidazol-5-yl}methylcarbonyl]-L-phenylalanine methyl ester

HRID 2254284Notes

Reaction equation

HRID 2254284 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:13]([CH2:14][C:15]([OH:17])=O)=[CH:12][N:11]=[C:10]1[S:18][CH2:19][CH2:20][CH3:21].OC1CC(=O)NC1=O.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[CH3:46][O:47][C:48](=[O:58])[C@H:49]([CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[NH2:50].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[CH3:46][O:47][C:48](=[O:58])[C@H:49]([CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[NH:50][C:15]([CH2:14][C:13]1[N:9]([CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:10]([S:18][CH2:19][CH2:20][CH3:21])=[N:11][CH:12]=1)=[O:17]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 181836963-Hydroxypyrrolidine-2,5-dioneHCID 193515541-(2-chlorophenyl)methyl-5-carboxymethyl-2-propylthio-1H-imidazole

Product 1

HCID 54145803N-[{1-(2-chlorophenyl)methyl-2-propylthio-1H-imidazol-5-yl}methylcarbonyl]-L-phenylalanine methyl esterYield 74.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[1-(2-chlorophenyl)methyl-2-propylthio-1H-imidazol-5-yl]acetic acid (0.52 g, 1.6 mmol) in tetrahydrofuran (20 mL) was stirred with N hydroxysuccinimide (0.203 g, 1.76 mmol) and dicyclohexylcarbodiimide (0.33 g, 0.16 mmol) for 30 minutes. Then L-phenylalanine methyl ester hydrochloride (0.449 g, 2.08 mmol) and triethylamine (0.21 g, 2.08 mmol) were added and the suspension was stirred at ambient temperature for 18 hours. The mixture was diluted with ethyl acetate, filtered and the concentrated filtrate was flash chromatographed over silica gel with 3:2 ethyl acetate/hexane to give 0.58 g (74%) of N-[{1-(2-chlorophenyl)methyl-2-propylthio-1H-imidazol-5-yl}methylcarbonyl]-L-phenylalanine methyl ester as an oil.

Workup

  1. filtrationfiltered
  2. customchromatographed over silica gel with 3:2 ethyl acetate/hexane

Sources & evidence

ORD record
ord-0ae44cdcbed64087b8ab3d50461045b4
Source dataset
uspto-grants-1993_08
Patent number
US05234917

Reaction notes

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