Lithium hydroxide, monohydrate → HCID 178452280, compound

HRID 1157799Notes

Reaction equation

F[C:2]1[N:7]=[C:6]([N:8]2[C:12]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)=[N:11][N:10]=[N:9]2)[CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].S(=O)(=O)(O)[O-:30].[Na+]>O1CCCC1.O>[OH:30][C:2]1[N:7]=[C:6]([N:8]2[C:12]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)=[N:11][N:10]=[N:9]2)[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Part C″: To a solution of tert-butyl 4-(1-(6-fluoropyridin-2-yl)-1H-tetrazol-5-yl)piperazine-1-carboxylate (0.349 g, 1.00 mmol) in 20 mL of tetrahydrofuran at 25° C. was added a solution of lithium hydroxide monohydrate (0.084 g, 2.00 mmol) in 5 mL of water, and the resulting mixture was stirred at 25° C. for 11 days. The reaction mixture was diluted with water, the pH of the solution was adjusted to ˜pH 6 employing aqueous sodium bisulfate solution, and the mixture was extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography on silica gel (elution: 0-50% diethyl ether/methylene chloride) to afford tert-butyl 4-(1-(6-hydroxypyridin-2-yl)-1H-tetrazol-5-yl)piperazine-1-carboxylate (0.090 g); Mass Spec.: m/e: 348.24 (M+H)+ [calc'd: 348.18]; 1H NMR (300 MHz, CDCl3) δ 7.84 (m, 1H), 7.21 (m, 1H), 6.89 (m, 1H), 3.52 (m, 4H), 3.32 (m, 4H), 1.45 (s, 9H).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe combined extracts were washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-1bc2ff6efbe8485d9bf2a334f2f0d5d9
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807676B2

Reaction notes

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