Hydrochloric Acid → 4-(Cyclopropylmethyl)-3-oxo-3,4-dihydropyrazine-2-carboxylic acid

HRID 1676342Notes

Reaction equation

HRID 1676342 reaction equation
[Li+].[OH-].[CH:3]1([CH2:6][N:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]([O:15]C)=[O:14])[C:8]2=[O:17])[CH2:5][CH2:4]1.Cl>C1COCC1.CO>[CH:3]1([CH2:6][N:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]([OH:15])=[O:14])[C:8]2=[O:17])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67349675Methyl 4-(cyclopropylmethyl)-3-oxo-3,4-dihydropyrazine-2-carboxylate

Product 1

HCID 673454214-(Cyclopropylmethyl)-3-oxo-3,4-dihydropyrazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

LiOH (0.84 mL, 0.84 mmol, 1.0 M) was added to a solution of methyl 4-(cyclopropylmethyl)-3-oxo-3,4-dihydropyrazine-2-carboxylate (87 mg, 0.42 mmol) in a mixture of THF-MeOH (3:1 ratio, 2 mL) at room temperature. After stirring for 2 hours, the reaction mixture was acidified to pH 1 with aq. 1N HCl solution (0.14 mL) and then concentrated to afford the desired product salt. 1H NMR (400 MHz, CD3OD) δ 7.67 (d, 1H), 7.37 (m, 1H), 3.86 (d, 2H), 1.32 (m, 1H), 0.61 (m, 2H), 0.45 (m, 2H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-6e31c5da0d754829971dfaf385ade190
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

Loading…