Trifluoroacetic acid → 2-Benzyl-8-hydroxy-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-7-carboxylic acid

HRID 747843Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]2[CH:14]=[C:15]([C:18]([O:20]CC)=[O:19])[C:16]([OH:17])=[C:10]2[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(C(F)(F)F)=O>C(O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]2[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[C:16]([OH:17])=[C:10]2[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl 2-benzyl-8-hydroxy-1-oxo-1,2,3,4-tetrahydropyrrolo-[1,2-α]pyrazine-7-carboxylate (0.30 g; see Example 1) and aqueous sodium hydroxide (1 M, 2 mL) in ethanol (20 mL) was heated in a sealed tube at 100° C. overnight. The product mixture was acidified with addition of TFA and concentrated under vacuum. The residue was subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound.

Workup

concentrationconcentrated under vacuum
customThe residue was subjected to HPLC purification on C-18 stationary phase
washeluted with water/acetonitrile/TFA mobile phase
customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record: ord-179fa5f3e89140d99f1084a3e534f503
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399763B2

Reaction notes

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