Triethylamine → Methyl N-[3-(4-i-Propylphenyl)acryloyl]-L-Tryptophanate

HRID 1746611Notes

Reaction equation

HRID 1746611 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.[CH:25]([C:28]1[CH:38]=[CH:37][C:31]([CH:32]=[CH:33][C:34](O)=[O:35])=[CH:30][CH:29]=1)([CH3:27])[CH3:26].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH:25]([C:28]1[CH:29]=[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]=1)([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 728543-(4-(1-Methylethyl)phenyl)-2-propenoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734891Methyl tryptophanate hydrochloride

Product 1

HCID 67130590Methyl N-[3-(4-i-Propylphenyl)acryloyl]-L-TryptophanateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The same procedures as in Example 146 were carried out from methyl L-tryptophanate hydrochloride (3.0 g), triethylamine (2.0 mL), 4-i-propylcinnamic acid (2.7 g), WSC.HCl (2.7 g), and methylene chloride (80 mL), to give the captioned compound (4.5 g, 98%) as an oily product.

Sources & evidence

ORD record
ord-e74e303125fa4ef1ade426eed71f05c6
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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