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

HRID 1746512Notes

Reaction equation

HRID 1746512 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.[F:24][C:25]1[CH:26]=[C:27]([CH:33]=[CH:34][CH:35]=1)[CH:28]=[CH:29][C:30](O)=[O:31].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[F:24][C:25]1[CH:26]=[C:27]([CH:28]=[CH:29][C:30]([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:31])[CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 886063-(3-Fluorophenyl)-2-propenoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69612215(S)-Methyl 2-amino-3-(4-methoxyphenyl)propanoate hydrochloride

Product 1

HCID 86655468Methyl N-[3-(3-Fluorophenyl)acryloyl]-O4-Methyl-L-TyrosinateYield 99.7%

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), 3-fluorocinnamic acid (1.6 g), WSC.HCl (1.9 g), and methylene chloride (60 mL), to give the captioned compound (2.9 g, 99%) as an oily product.

Sources & evidence

ORD record
ord-6f1ccc800de348b59278649c6932bdc4
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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