Citric Acid → HCID 66851504, compound

HRID 1466602Notes

Reaction equation

[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[C:17]([C:18]([O-:20])=[O:19])=[C:12]2[N:13]=[CH:14][CH:15]=[CH:16][N:11]2[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[C:17]([C:18]([OH:20])=[O:19])=[C:12]2[N:13]=[CH:14][CH:15]=[CH:16][N:11]2[N:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-(bis(tert-butoxycarbonyl)amino)pyrazolo[1,5-a]pyrimidine-3-carboxylate (220 mg, 0.54 mmol) in ethanol (15 mL) was added 4 mL of a 10% aqueous lithium hydroxide solution. The reaction mixture was heated to 70° C. for 18 hrs, then cooled to room temperature. 15 mL of a 10% aqueous solution of citric acid was added and the reaction mixture concentrated in vacuo. The residue was partitioned between EtOAc and a saturated aqueous solution of citric acid, then the organic layer was washed with water and brine, then dried over Na2SO4, filtered and concentrated in vacuo to afford 150 mg of 2-(tert-butoxycarbonylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid. 1H NMR (400 MHz, DMSO) δ 9.34 (s, 1H), 9.12 (dd, J=6.9, 1.7, 1H), 8.71 (dd, J=4.3, 1.7, 1H), 7.20 (dd, J=6.9, 4.3, 1H), 1.49 (s, 9H).

Workup

temperaturecooled to room temperature
concentrationthe reaction mixture concentrated in vacuo
customThe residue was partitioned between EtOAc
washa saturated aqueous solution of citric acid, then the organic layer was washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a67359ea06704ae6913605fac6cf3a16
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999998B2

Reaction notes

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