Triethylamine → HCID 68578347, compound

HRID 642808Notes

Reaction equation

HRID 642808 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][CH:18]([C:23]3[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=3)[CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:39][O:40][C:41](=[O:45])[CH2:42][CH2:43][NH2:44].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:39][O:40][C:41](=[O:45])[CH2:42][CH2:43][NH:44][C:27](=[O:28])[C:26]1[CH:25]=[CH:24][C:23]([CH:18]([NH:17][C:14]2[CH:15]=[CH:16][C:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:10][CH:9]=3)=[CH:12][CH:13]=2)[CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 192794Methyl beta-alanateHCID 67485985HCID 67485985, compound

Product 1

HCID 68578347HCID 68578347, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[1-(4′-tert-butyl-biphenyl-4-ylamino)-3-methyl-butyl]-benzoic acid (310 mg, 0.75 mmol) in methylene chloride (7 mL) are added triethyl amine (0.31 mL, 2.24 mmol), DMAP (5.0 mg), 3-amino-propionic acid methyl ester (156 mg, 1.12 mmol) and EDCI (431 mg, 2.24 mmol) at room temperature. The reaction mixture is stirred at room temperature overnight, loaded on silica gel, and eluted with hexanes using a gradient from 0-100% ethyl acetate to provide 230 mg of the titled compound as a white solid. 1H-NMR.

Workup

  1. washeluted with hexanes using a gradient from 0-100% ethyl acetate

Sources & evidence

ORD record
ord-04d1bad050424b22b285244587aad6eb
Source dataset
uspto-grants-2010_04
Patent number
US07696248B2

Reaction notes

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