Triethylamine → Methyl 1-Methyl-Nalpha-[3-(4-Phenoxyphenyl)acryloyl]-L-Tryptophanate

HRID 1746501Notes

Reaction equation

HRID 1746501 reaction equation
Cl.[CH3:2][N:3]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:5]([CH2:6][C@@H:7]([C:9]([O:11][CH3:12])=[O:10])[NH2:8])=[CH:4]1.C(N(CC)CC)C.[O:26]([C:33]1[CH:43]=[CH:42][C:36]([CH:37]=[CH:38][C:39](O)=[O:40])=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH3:2][N:3]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:5]([CH2:6][C@@H:7]([C:9]([O:11][CH3:12])=[O:10])[NH:8][C:39](=[O:40])[CH:38]=[CH:37][C:36]2[CH:42]=[CH:43][C:33]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:34][CH:35]=2)=[CH:4]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 209923884-Phenoxycinnamic acidHCID 67130420methyl (2S)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoate hydrochloride

Product 1

HCID 86655459Methyl 1-Methyl-Nalpha-[3-(4-Phenoxyphenyl)acryloyl]-L-TryptophanateYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The same procedures as in Example 2 were carried out from the compound obtained in Example 20 (1.0 g), triethylamine (0.54 mL), 4-phenoxycinnamic acid (0.94 g), WSC.HCl (0.75 g), and methylene chloride (40 mL), to give the captioned compound (0.93 g, 55%) as an oily product.

Sources & evidence

ORD record
ord-9bfabcbe7dd8410fb13ec4ecc611b36f
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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