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

HRID 1746497Notes

Reaction equation

HRID 1746497 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.[F:26][C:27]1[CH:37]=[CH:36][C:30]([CH:31]=[CH:32][C:33](O)=[O:34])=[CH:29][CH:28]=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[F:26][C:27]1[CH:28]=[CH:29][C:30]([CH:31]=[CH:32][C:33]([NH:8][C@H:7]([C:9]([O:11][CH3:12])=[O:10])[CH2:6][C:5]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:3]([CH3:2])[CH:4]=2)=[O:34])=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 980703-(4-Fluorophenyl)-2-propenoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67130420methyl (2S)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoate hydrochloride

Product 1

HCID 86655455Methyl Nalpha-[3-(4-Fluorophenyl)acryloyl]-1-Methyl-L-TryptophanateYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The same procedures as in Example 2 were carried out from the compound obtained in Example 20 (2.0 g), triethylamine (1.1 mL), 4-fluorocinnamic acid (1.4 g), WSC.HCl (1.6 g), and methylene chloride (80 mL), to give the captioned compound (2.7 g, 94%) as an oily product.

Sources & evidence

ORD record
ord-f2e0d598940240fbaf806a425ec3a9ca
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

Loading…