Potassium Carbonate → (R)-9-methyl-6-oxo-6,7,8,9-tetrahydropyrido[3',2':4,5]pyrrolo[1,2-a]pyrazine-2-carboxylic acid

HRID 1521725Notes

Reaction equation

[NH2:1][CH2:2][C@@H:3]([N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16]CC)=[O:15])=[CH:12][CH:13]=[C:8]2[CH:7]=[C:6]1[C:19]([O:21]CC)=O)[CH3:4].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:4][C@H:3]1[N:5]2[C:9]3[N:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=[CH:13][C:8]=3[CH:7]=[C:6]2[C:19](=[O:21])[NH:1][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of diethyl 1-[(2S)-1-aminopropan-2-yl]-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (2.17 g, 6.80 mmol) in ethanol (40 mL) is added potassium carbonate (2.82 g, 20.4 mmol). The mixture is stirred at 60° C. for 16 h and is then cooled to room temperature. The ethanol is removed in vacuo and the aqueous mixture is acidified to pH 5 with 1N aqueous hydrochloric acid. The resulting solid is collected by filtration and dried in vacuo to afford the title compound as a pale yellow solid (1.40 g, 84%). LCMS: 246.64 (M+H+).

Workup

temperatureis then cooled to room temperature
customThe ethanol is removed in vacuo
filtrationThe resulting solid is collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-ea1b68ea6c25448b91fb878428516378
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073926B2

Reaction notes

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