Lithium Hydroxide → HCID 58826332, compound

HRID 1172367Notes

Reaction equation

HRID 1172367 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][C@@H:12]([NH:17][C:18]([N:20]2[CH2:25][CH2:24][CH:23]([C:26]3[C:27](=[O:36])[NH:28][C:29]4[C:34]([CH:35]=3)=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:22][CH2:21]2)=[O:19])[C:13]([O:15]C)=[O:14])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[OH-].[Li+]>C1COCC1.O>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][C@@H:12]([NH:17][C:18]([N:20]2[CH2:21][CH2:22][CH:23]([C:26]3[C:27](=[O:36])[NH:28][C:29]4[C:34]([CH:35]=3)=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:24][CH2:25]2)=[O:19])[C:13]([OH:15])=[O:14])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58826320HCID 58826320, compound

Product 1

HCID 58826332HCID 58826332, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-methyl 3-(7-methyl-1H-indazol-5-yl)-2-(4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxamido)propanoate (2.44 g, 5 mmol) in THF (50 mL) was added a solution of lithium hydroxide (420 mg, 10 mmol) in water (15 mL) at room temperature. After 1 h, most of the THF was removed and neutralized with 1.0 M hydrogen chloride to give (R)-3-(7-methyl-1H-indazol-5-yl)-2-(4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxamido)propanoic acid as a white solid in 95% yield. 1H-NMR (CD3OD) δ 7.97 (s, 1H), 7.66 (d, J=8 Hz, 1H), 7.60 (s, 1H), 7.51-7.48 (m, 2H), 7.33 (d, J=8 Hz, 1H), 7.27-7.24 (m, 1H), 7.12 (s, 1H), 4.61-4.58 (m, 1H), 4.14-4.08 (m, 2H), 3.76-3.73 (m, 2H), 3.13-2.84 (m, 4H), 2.54 (s, 3H), 1.90-1.84 (m, 4H), 1.48-1.34 (m, 2H); MS (ESI) 474 (M+H) ; Rf=1.89.

Workup

  1. custommost of the THF was removed

Sources & evidence

ORD record
ord-39cc0971e7aa471ea08b16d507cefd39
Source dataset
uspto-grants-2010_11
Patent number
US07834007B2

Reaction notes

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