Hydrochloric Acid → N-(Pyrazinylcarbonyl)-L-phenylalanine
Reaction equation
C[O:2][C:3](=[O:21])[C@H:4]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:5][C:6]([C:8]1[CH:13]=[N:12][CH:11]=[CH:10][N:9]=1)=[O:7].[OH-].[Na+].Cl>CC(C)=O>[N:9]1[CH:10]=[CH:11][N:12]=[CH:13][C:8]=1[C:6]([NH:5][C@H:4]([C:3]([OH:21])=[O:2])[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The product N-pyrazineformyl-L-phenylalanine methyl ester (1.0 g, 3.51 mmol) in Preparation example 2 was dissolved with 10 ml of acetone, 2N NaOH was added dropwise slowly until a pH value of 12˜13 was obtained, and the solution was kept reacting under the condition of ice water bath, the reaction was monitored by TLC and completed after 2 h. Hydrochloric acid was add dropwise under the condition of ice water bath until a pH value of 2˜3 was obtained, a large amount of white solid was produced, the generated precipitate was filtered, washed with water and diethyl ether followed by airing to dry and gave 0.89 g of white product with a yield of 93.6%, m.p.: 166-169° C. 1H-NMR (DMSO-d6, 300 MHz): δ 3.23 (—CH2, m, 2H), 4.74 (—CH, m, 1H), 7.16˜7.25 (-Ph, m, 5H), 8.74 (—CONH, t, 1H), 8.86˜8.89 (-Pyz, t, 2H), 9.14 (-Pyz, d, 1H), 13.06 (—COOH, s, 1H).
Workup
- additionwas added dropwise slowly until a pH value of 12˜13
- customwas obtained
- customthe solution was kept reacting under the condition of ice water bath
- customwas obtained
- customa large amount of white solid was produced
- filtrationthe generated precipitate was filtered
- washwashed with water and diethyl ether
- customto dry
Sources & evidence
- ORD record
- ord-51cdaf540b29414cb6408e4d1fff3872
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09421237B2
Reaction notes
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