Triethylamine → Methyl Nalpha-[3-(2,6-Difluorophenyl)acryloyl]-L-Tryptophanate

HRID 1746487Notes

Reaction equation

HRID 1746487 reaction equation
Cl.[NH2:2][C@H:3]([C:14]([O:16][CH3:17])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.C(N(CC)CC)C.[F:25][C:26]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:27]=1[CH:28]=[CH:29][C:30](O)=[O:31].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[F:25][C:26]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:27]=1[CH:28]=[CH:29][C:30]([NH:2][C@H:3]([C:14]([O:16][CH3:17])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 517784(2E)-3-(2,6-difluorophenyl)acrylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734891Methyl tryptophanate hydrochloride

Product 1

HCID 86655446Methyl Nalpha-[3-(2,6-Difluorophenyl)acryloyl]-L-TryptophanateYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The same procedures as in Example 2 were carried out from methyl L-tryptophanate hydrochloride (3.0 g), triethylamine (2.0 mL), 2,6-difluorocinnamic acid (2.6 g), WSC.HCl (2.7 g), and methylene chloride (80 mL), to give the captioned compound (3.9 g, 85%) as an oily product.

Sources & evidence

ORD record
ord-afaa3f935ba74cc9ab8bfece839d5f74
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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