Triethylamine → Methyl N-[3-(2-Cyanophenyl)acryloyl]-O4-Methyl-L-Tyrosinate

HRID 1746515Notes

Reaction equation

HRID 1746515 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][C@@H:9]([C:11]([O:13][CH3:14])=[O:12])[NH2:10])=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:24]([C:26]1[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=1[CH:28]=[CH:29][C:30](O)=[O:31])#[N:25].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:24]([C:26]1[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=1[CH:28]=[CH:29][C:30]([NH:10][C@H:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:16][CH:15]=1)=[O:31])#[N:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2648073-(2-Cyanophenyl)prop-2-enoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69612215(S)-Methyl 2-amino-3-(4-methoxyphenyl)propanoate hydrochloride

Product 1

HCID 86655471Methyl N-[3-(2-Cyanophenyl)acryloyl]-O4-Methyl-L-TyrosinateYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The same procedures as in Example 2 were carried out from the compound obtained in Example 33 (2.5 g), triethylamine (1.7 mL), 2-cyanocinnamic acid (2.1 g), WSC.HCl (2.3 g), and methylene chloride (70 mL), to give the captioned compound (3.2 g, 86%) as crystals.

Sources & evidence

ORD record
ord-4baea92b42464b00b79b3eae806bd304
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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