Triethylamine → Methyl Nalpha-[3-(2,4-Difluorophenyl)acryloyl]-1-Methyl-L-Tryptophanate

HRID 1746499Notes

Reaction equation

HRID 1746499 reaction equation
Cl.[CH3:2][N:3]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:5]([CH2:6][C@@H:7]([C:9]([O:11][CH3:12])=[O:10])[NH2:8])=[CH:4]1.C(N(CC)CC)C.[F:26][C:27]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:28]=1[CH:29]=[CH:30][C:31](O)=[O:32].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[F:26][C:27]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:28]=1[CH:29]=[CH:30][C:31]([NH:8][C@H:7]([C:9]([O:11][CH3:12])=[O:10])[CH2:6][C:5]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]([CH3:2])[CH:4]=1)=[O:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6035023-(2,4-Difluorophenyl)acrylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67130420methyl (2S)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoate hydrochloride

Product 1

HCID 86655457Methyl Nalpha-[3-(2,4-Difluorophenyl)acryloyl]-1-Methyl-L-TryptophanateYield 49.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The same procedures as in Example 2 were carried out from the compound obtained in Example 20 (1.0 g), triethylamine (0.54 mL), 2,4-difluorocinnamic acid (0.72 g), WSC.HCl (0.75 g), and methylene chloride (40 mL), to give the captioned compound (0.73 g, 49%) as an oily product.

Sources & evidence

ORD record
ord-eec5d4fada9e4338bfdf63579f008293
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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