Triethylamine → HCID 67153566, compound

HRID 1914304Notes

Reaction equation

HRID 1914304 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]([C:17]2[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=2)[CH2:10][CH:11]([CH3:16])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:33][O:34][C:35](=[O:39])[CH2:36][CH2:37][NH2:38].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:33][O:34][C:35](=[O:39])[CH2:36][CH2:37][NH:38][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:17]([CH:9]([S:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH2:10][CH:11]([CH3:16])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 192794Methyl beta-alanateHCID 67153417HCID 67153417, compound

Product 1

HCID 67153566HCID 67153566, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[1-(4-bromo-phenylsulfanyl)-3-methyl-heptyl]benzoic acid (1700 mg, 4.18 mmol) in methylene chloride (42 mL) are added triethyl amine (1.75 mL, 12.53 mmol), DMAP (5.0 mg), 3-amino-propionic acid methyl ester (875 mg, 6.27 mmol) and EDCI (2408 mg, 12.53 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 3-{4-[1-(4-bromo-phenylsulfanyl)-3-methyl-heptyl]-benzoylamino}-propionic acid methyl ester (1.640 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-9c20806b7a054eb2be8a9ebf2b268c8f
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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