Lithium Hydroxide → 2-(4-((tert-butoxycarbonyl)amino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoic acid

HRID 1477895Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[C:18]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)([CH2:23][CH3:24])[C:19]([O:21]C)=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>O1CCOCC1.O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[C:18]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)([CH2:23][CH3:24])[C:19]([OH:21])=[O:20])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

Methyl 2-(4-((tert-butoxycarbonyl)amino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoate (0.5 g, 1.13 mmol) (enantiomer A intermediate), as described in example 18 step D, as described in Example 18 step D, was dissolved in a mixture of 1,4-dioxane (1.0 mL) and water (0.25 mL) followed by addition of LiOH (0.27 g, 11.26 mmol). The mixture was stirred at 70° C. for 5 hours, then concentrated to remove solvent. The residue was dissolved in water (20 mL) and acidified with 1 N aq. HCl solution (11.3 mL) to give white precipitate. The solid was filtered, washed with water, and dried under vacuum to give title compound. LC/MS m/z=430.1[M+H]+.

Workup

concentrationconcentrated
customto remove solvent
dissolutionThe residue was dissolved in water (20 mL)
customto give white precipitate
filtrationThe solid was filtered
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-91f7535e6a3b41f086823b6dff9eacbd
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403807B2

Reaction notes

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