Triethylamine → HCID 67153603, compound

HRID 1914294Notes

Reaction equation

HRID 1914294 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]([C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=2)[CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:30][O:31][C:32](=[O:36])[CH2:33][CH2:34][NH2:35].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:30][O:31][C:32](=[O:36])[CH2:33][CH2:34][NH:35][C:18](=[O:19])[C:17]1[CH:16]=[CH:15][C:14]([CH:9]([S:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 192794Methyl beta-alanateHCID 67153413HCID 67153413, compound

Product 1

HCID 67153603HCID 67153603, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[1-(4-bromo-phenylsulfanyl)-3-methyl-butyl]-benzoic acid (379 mg, 1 mmol) in methylene chloride (10 mL) are added triethyl amine (0.42 mL, 3 mmol), DMAP (5.0 mg), 3-amino-propionic acid methyl ester (209 mg, 1.5 mmol) and EDCI (577 mg, 3.0 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-butyl]-benzoylamino}-propionic acid methyl ester (350 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-1199f0fee2c240e89a04086f51ed1bcc
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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