Triethylamine → HCID 67153406, compound

HRID 1914312Notes

Reaction equation

HRID 1914312 reaction equation
[Br:1][C:2]1[C:24]([CH3:25])=[CH:23][C:5]([O:6][CH:7]([C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:4][C:3]=1[CH3:26].C(N(CC)CC)C.[CH3:34][O:35][C:36](=[O:40])[CH2:37][CH2:38][NH2:39].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:34][O:35][C:36](=[O:40])[CH2:37][CH2:38][NH:39][C:18](=[O:19])[C:17]1[CH:16]=[CH:15][C:14]([CH:7]([O:6][C:5]2[CH:23]=[C:24]([CH3:25])[C:2]([Br:1])=[C:3]([CH3:26])[CH:4]=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 67153518HCID 67153518, compound

Product 1

HCID 67153406HCID 67153406, compoundYield 43.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[1-(4-bromo-3,5-dimethyl-phenoxyl)-heptyl]-benzoic acid (1790 mg, 4.27 mmol) in methylene chloride (43 mL) are added triethyl amine (1.79 mL, 12.82 mmol), DMAP (5.0 mg), 3-amino-propionic acid methyl ester (895 mg, 6.4 mmol) and EDCI (2463 mg, 12.8 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-3,5-dimethyl-phenoxyl)-heptyl]-benzoylamino}-propionic acid methyl ester (945 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-f6e1f7746c054738b6188575d9006e45
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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