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

HRID 1746480Notes

Reaction equation

HRID 1746480 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.[C:25]([O:28][C:29]1[CH:39]=[CH:38][C:32]([CH:33]=[CH:34][C:35](O)=[O:36])=[CH:31][CH:30]=1)(=[O:27])[CH3:26].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:25]([O:28][C:29]1[CH:39]=[CH:38][C:32]([CH:33]=[CH:34][C:35]([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:36])=[CH:31][CH:30]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 85857Cinnamic acid, p-hydroxy-, acetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734891Methyl tryptophanate hydrochloride

Product 1

HCID 86655439Methyl Nalpha-[3-(4-Acetoxyphenyl)acryloyl]-L-TryptophanateYield 94%

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-acetoxycinnamic acid (2.9 g), WSC.HCl (2.7 g), and methylene chloride (80 mL), to give the captioned compound (4.5 g, 93%) as an oily product.

Sources & evidence

ORD record
ord-d26219ef941d4825b25adf0612a1a3a3
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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