Hydrochloric Acid → Methyl N-((6-chloro-4-hydroxy-2-oxo-spiro[naphthalene-1,4'-piperidin]-3-yl)carbonyl)glycinate

HRID 1868869Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:21](=[CH:22][CH:23]=1)[C:8]1([CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1)[C:7](=[O:24])[C:6]([C:25]([NH:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[O:26])=[C:5]2[OH:33].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:21](=[CH:22][CH:23]=1)[C:8]1([CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1)[C:7](=[O:24])[C:6]([C:25]([NH:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[O:26])=[C:5]2[OH:33]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of methyl N-((6-chloro-4-hydroxy-2-oxo-1′-(tert-butoxycarbonyl)-spiro[naphthalene-1,4′-piperidin]-3-yl)carbonyl)glycinate (333 mg, 695 μmol) in dioxane (10 mL) was treated with HCl (4.0M in 1,4-dioxane (1738 μL, 6953 μmol)). The reaction was stirred at 23° C. After 20 hours, the reaction was concentrated in vacuo affording 231 mg of the title compound as the hydrochloride salt. MS m/e=379.2 (M+H)+.

Workup

concentrationthe reaction was concentrated in vacuo

Sources & evidence

ORD record: ord-73aec1842afa4730bdcff9c9e53f2dd4
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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