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

HRID 1746479Notes

Reaction equation

HRID 1746479 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:30]=[C:31]([CH:37]=[CH:38][CH:39]=1)[CH:32]=[CH:33][C:34](O)=[O:35])(=[O:27])[CH3:26].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:25]([O:28][C:29]1[CH:30]=[C:31]([CH:32]=[CH:33][C:34]([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:35])[CH:37]=[CH:38][CH:39]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1406792-Propenoic acid, 3-[3-(acetyloxy)phenyl]-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734891Methyl tryptophanate hydrochloride

Product 1

HCID 86655438Methyl Nalpha-[3-(3-Acetoxyphenyl)acryloyl]-L-TryptophanateYield 98.2%

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), 3-acetoxycinnamic acid (2.9 g), WSC.HCl (2.7 g), and methylene chloride (80 mL), to give the captioned compound (4.7 g, 98%) as an amorphous solid.

Sources & evidence

ORD record
ord-cc8dbd6f901f40cfb8ddccfb59bc19f8
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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