Lithium hydroxide, monohydrate → N-((6-Chloro-4-hydroxy-2-oxo-1'-(phenylcarbonyl)-spiro[naphthalene-1,4'-piperidin]-3-yl)carbonyl)glycine

HRID 1868871Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:22](=[CH:23][CH:24]=1)[C:8]1([CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])[CH2:10][CH2:9]1)[C:7](=[O:25])[C:6]([C:26]([NH:28][CH2:29][C:30]([O:32]C)=[O:31])=[O:27])=[C:5]2[OH:34].O.[OH-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:22](=[CH:23][CH:24]=1)[C:8]1([CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])[CH2:10][CH2:9]1)[C:7](=[O:25])[C:6]([C:26]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:27])=[C:5]2[OH:34]

Participants

Conditions

Temperature: 25 °C

Procedure

The ester was treated with lithium hydroxide hydrate (0.025 g, 0.60 mmol) in THF (1.4 mL) and water (0.6 mL) and stirred at 25° C. for 30 minutes. The reaction was quenched with Dowex 50 (W×8) acidic resin (prewashed with MeOH) to pH<4.0 and filtered. The filtrate was concentrated and azeotroped with toluene (2×5 mL), to give the title compound (0.017 g). MS m/e=469.5 (M+H)+. Calculated for C24H21ClN2O6 468.11.

Workup

customThe reaction was quenched with Dowex 50 (W×8) acidic resin (prewashed with MeOH) to pH<4.0
filtrationfiltered
concentrationThe filtrate was concentrated
customazeotroped with toluene (2×5 mL)

Sources & evidence

ORD record: ord-a5695b5d05624378aab8631bac4c20ea
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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