Hydrochloric Acid → 4-Oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-methyl ester

HRID 417446Notes

Reaction equation

HRID 417446 reaction equation
O.[OH-].[Li+].[CH3:4][O:5][C:6]([N:8]1[CH2:13][C:12](=[O:14])[N:11]2[CH:15]([C:18]([O:20]CC)=[O:19])[CH2:16][CH2:17][CH:10]2[CH2:9]1)=[O:7].Cl>O.CO.O1CCCC1>[CH3:4][O:5][C:6]([N:8]1[CH2:13][C:12](=[O:14])[N:11]2[CH:15]([C:18]([OH:20])=[O:19])[CH2:16][CH2:17][CH:10]2[CH2:9]1)=[O:7]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 666205494-Oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 6-ethyl ester 2-methyl ester

Product 1

HCID 666208694-Oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-methyl esterYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (16.8 mg, 0.38 mmol) in water (0.5 mL) was added to a solution of 4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 6-ethyl ester 2-methyl ester (86 mg, 0.32 mmol) in methanol (1 mL) and tetrahydrofuran (1 mL). After 2 hours, an aqueous solution of hydrogen chloride (1N, 0.41 mL, 0.41 mmol) was added and the organic solvents were removed under reduced pressure. The resulting aqueous solution was lyophilized for 16 hours to give 4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-methyl ester. A yield of 100% was assumed for the subsequent step. C10H14N2O5 calculated 242.1, observed [M+1]+ 242.9, [M+1]− 241.1; rt=1.54 min.

Workup

  1. customthe organic solvents were removed under reduced pressure
  2. waitThe resulting aqueous solution was lyophilized for 16 hours

Sources & evidence

ORD record
ord-1b90342d5e8e43d88a3afc094ba23d3d
Source dataset
uspto-grants-2012_01
Patent number
US08088368B2

Reaction notes

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