Methyl 9-benzyloxy-2-(3-chlorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylate → 9-benzyloxy-2-(3-chlorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylic acid

HRID 1349498Notes

Reaction equation

HRID 1349498 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:32])[C:11]([C:28]([O:30]C)=[O:29])=[CH:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:15](=[O:27])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.O.[OH-].[Li+]>[CH2:1]([O:8][C:9]1[C:10](=[O:32])[C:11]([C:28]([OH:30])=[O:29])=[CH:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:15](=[O:27])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 23077483Methyl 9-benzyloxy-2-(3-chlorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylate

Product 1

HCID 230775239-benzyloxy-2-(3-chlorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylic acidYield 86.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 9-benzyloxy-2-(3-chlorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylate (420 mg) was dissolved in tetrahydrofuran (8 ml)-water (2 ml), and 4N aqueous lithium hydroxide solution (0.58 ml) was added with stirring. After stirring at 70° C. for 1 hr, the mixture was concentrated. Water (5 ml) and then 5% aqueous potassium hydrogen sulfate solution (15 ml) were added with stirring. The precipitated crystals were collected by filtration to give 9-benzyloxy-2-(3-chlorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylic acid (352 mg).

Workup

  1. additionwas added
  2. stirringAfter stirring at 70° C. for 1 hr
  3. concentrationthe mixture was concentrated
  4. additionWater (5 ml) and then 5% aqueous potassium hydrogen sulfate solution (15 ml) were added
  5. stirringwith stirring
  6. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-a9aae6de6b7a469ca2c5b42707bf49e1
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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