Triethylamine → HCID 67343693, compound

HRID 1669321Notes

Reaction equation

HRID 1669321 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]([C:17]2[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=2)=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].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]([C:10]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Br:1])[CH:3]=2)=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 192794Methyl beta-alanateHCID 67343316HCID 67343316, compound

Product 1

HCID 67343693HCID 67343693, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[1-(3-bromo-4-methoxy-phenyl)-hept-1-enyl]-benzoic acid (380 mg, 0.94 mmol) in methylene chloride (9 mL) are added triethyl amine (0.39 mL, 2.81 mmol), DMAP (5.0 mg), 3-amino-propionic acid methyl ester (197 mg, 1.41 mmol) and EDCI (541 mg, 2.81 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 the titled compound (321 mg).

Workup

  1. washeluted
  2. washwith eluted with hexanes with a gradient from 0% of ethyl acetate to 100% of ethyl acetate giving the titled compound (321 mg)

Sources & evidence

ORD record
ord-6b1c33c5e80c4490856e77455c8139c4
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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