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

HRID 1746491Notes

Reaction equation

HRID 1746491 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.[O:25]([C:32]1[CH:42]=[CH:41][C:35]([CH:36]=[CH:37][C:38](O)=[O:39])=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[O:25]([C:32]1[CH:33]=[CH:34][C:35]([CH:36]=[CH:37][C:38]([NH:2][C@H:3]([C:14]([O:16][CH3:17])=[O:15])[CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH:6]=2)=[O:39])=[CH:41][CH:42]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734891Methyl tryptophanate hydrochlorideHCID 209923884-Phenoxycinnamic acid

Product 1

HCID 86655450Methyl Nalpha-[3-(4-Phenoxyphenyl)acryloyl]-L-TryptophanateYield 94.4%

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), 4-phenoxycinnamic acid (3.4 g), WSC.HCl (2.7 g, 14.1 mmol), and methylene chloride (80 mL), to give the captioned compound (4.9 g, 94%) as an oily product.

Sources & evidence

ORD record
ord-ab1390ae153b4e3eb25517a1cc9cc25d
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

Loading…