Triethylamine → 3-{4-[1-(4-Bromo-phenoxy)-heptyl]-benzoylamino}-propionic acid methyl ester

HRID 1160895Notes

Reaction equation

HRID 1160895 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH:7]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:32][O:33][C:34](=[O:38])[CH2:35][CH2:36][NH2:37].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:32][O:33][C:34](=[O:38])[CH2:35][CH2:36][NH:37][C:18](=[O:20])[C:17]1[CH:16]=[CH:15][C:14]([CH:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:24][CH:23]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 192794Methyl beta-alanateHCID 671534294-[1-(4-Bromo-phenoxyl)-heptyl]-benzoic acid

Product 1

HCID 671533873-{4-[1-(4-Bromo-phenoxy)-heptyl]-benzoylamino}-propionic acid methyl esterYield 80.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[1-(4-bromo-phenoxyl)-heptyl]-benzoic acid (1700 mg, 4.35 mmol) in methylene chloride (43 mL) are added triethyl amine (1.82 mL, 13.4 mmol), DMAP (5.0 mg), 3-amino-propionic acid methyl ester (910 mg, 6.52 mmol) and EDCI (2507 mg, 13.04 mmol) at room temperature. The reaction mixture is stirred at room temperature overnight, loaded on silica gel, eluted with eluted with hexanes with a gradient from 0% of ethyl acetate to 100% of ethyl acetate giving racemic 3-{4-[1-(4-bromo-phenoxyl)-heptyl]-benzoylamino}-propionic acid methyl ester (1660 mg).

Workup

  1. washeluted
  2. washwith eluted with hexanes with a gradient from 0% of ethyl acetate to 100% of ethyl acetate

Sources & evidence

ORD record
ord-20e0fa61f88a43ef913bd2588ef187bd
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

Loading…