Triethylamine → Methyl N-[3-(4-Acetoxyphenyl)acryloyl]-O4-Methyl-L-Tyrosinate

HRID 1746510Notes

Reaction equation

HRID 1746510 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]([O:27][C:28]1[CH:38]=[CH:37][C:31]([CH:32]=[CH:33][C:34](O)=[O:35])=[CH:30][CH:29]=1)(=[O:26])[CH3:25].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:24]([O:27][C:28]1[CH:38]=[CH:37][C:31]([CH:32]=[CH:33][C:34]([NH:10][C@H:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:16][CH:15]=2)=[O:35])=[CH:30][CH:29]=1)(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 85857Cinnamic acid, p-hydroxy-, acetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69612215(S)-Methyl 2-amino-3-(4-methoxyphenyl)propanoate hydrochloride

Product 1

HCID 86655466Methyl N-[3-(4-Acetoxyphenyl)acryloyl]-O4-Methyl-L-TyrosinateYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The same procedures as in Example 2 were carried out from the compound obtained in Example 33 (2.0 g), triethylamine (1.4 mL), 4-acetoxycinnamic acid (2.0 g), WSC.HCl (1.9 g), and methylene chloride (60 mL), to give the captioned compound (2.6 g, 79%) as crystals.

Sources & evidence

ORD record
ord-99ef783e09d944c2b2257f772ab21e82
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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