Triethylamine → Methyl N-{3-[3,5-Bis(trifluoromethyl)phenyl]acryloyl}-O4-Methyl-L-Tyrosinate

HRID 1746522Notes

Reaction equation

HRID 1746522 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]([F:42])([F:41])[C:26]1[CH:27]=[C:28]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH:29]=[CH:30][C:31](O)=[O:32].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[F:24][C:25]([F:41])([F:42])[C:26]1[CH:27]=[C:28]([CH:29]=[CH:30][C:31]([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:32])[CH:34]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:36]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27732123,5-Bis(trifluoromethyl)cinnamic acidHCID 69612215(S)-Methyl 2-amino-3-(4-methoxyphenyl)propanoate hydrochloride

Product 1

HCID 86655477Methyl N-{3-[3,5-Bis(trifluoromethyl)phenyl]acryloyl}-O4-Methyl-L-TyrosinateYield 70.3%

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), 3,5-bis(trifluoromethyl)cinnamic acid (3.5 g), WSC.HCl (2.3 g), and methylene chloride (70 mL), to give the captioned compound (3.4 g, 70%) as an oily product.

Sources & evidence

ORD record
ord-6e72337e11e94a329ee687d40a1006fc
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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