Water → N-(Pyrazinylcarbonyl)-L-phenylalanine

HRID 335380Notes

Reaction equation

HRID 335380 reaction equation
[C:1]1([CH2:7][C@H:8]([NH:13][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[O:15])[C:9]([O:11]C)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C(N(CC)CC)C.[Li+].[Br-]>C(#N)C>[C:1]1([CH2:7][C@H:8]([NH:13][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[O:15])[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 82050Lithium BromideHCID 1258094473058-37-4

Product 1

HCID 15042559N-(Pyrazinylcarbonyl)-L-phenylalanine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve (S)-Methyl 3-phenyl-2-(pyrazine-2-carboxamido)propanoate (57.65 g) in 572 ml of acetonitrile and add 11.7 ml water and 84 ml of triethylamine. Cool the reaction mixture to 0° C. on ice bath and add 175.0 g of LiBr in several portions at vigorous stirring. After 10 minutes of stirring, increase the temperature to ambient temperature. (NB. A HPLC sample showed 99.97% conversion with 98.78% content of the desired product).

Workup

  1. temperatureincrease the temperature to ambient temperature

Sources & evidence

ORD record
ord-f6dcf495aa434736b4964ee0c80be9a9
Source dataset
uspto-grants-2014_11
Patent number
US08884009B2

Reaction notes

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