Triethylamine → methyl 3-hydroxy-3-[4-[2-[N-(3-pyridylmethyl)carbamoyl]ethenyl]phenyl]propionate

HRID 2227498Notes

Reaction equation

HRID 2227498 reaction equation
[OH:1][CH:2]([C:8]1[CH:18]=[CH:17][C:11]([CH:12]=[CH:13][C:14]([OH:16])=O)=[CH:10][CH:9]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C.[NH2:36][CH2:37][C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1>CN(C)C=O>[OH:1][CH:2]([C:8]1[CH:9]=[CH:10][C:11]([CH:12]=[CH:13][C:14](=[O:16])[NH:36][CH2:37][C:38]2[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=2)=[CH:17][CH:18]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 310183-PyridinemethanamineHCID 76257Diethyl cyanophosphonateHCID 701562264-[1-Hydroxy-2-(methoxycarbonyl)ethyl]cinnamic acid

Product 1

HCID 70156661methyl 3-hydroxy-3-[4-[2-[N-(3-pyridylmethyl)carbamoyl]ethenyl]phenyl]propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Finally, 82 mg of 4-[1-hydroxy-2-(methoxycarbonyl)ethyl]cinnamic acid was dissolved in 37 μl 3-(aminomethyl)pyridine and 1 ml dimethylformamide, and then treated with 55 μl diethyl cyanophosphate and 50 μl triethylamine on ice for 1 hour to give methyl 3-hydroxy-3-[4-[2-[N-(3-pyridylmethyl)carbamoyl]ethenyl]phenyl]propionate of interest (17 mg, 15%) as an amorphous solid.

Sources & evidence

ORD record
ord-2013fe07e8eb47299b2118af8c06cf37
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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