1,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-2-oxo-6-(3-pyridinyl)-naphthalen-3-yl)carbonyl)glycinate → N-((4-Hydroxy-1,1-dimethyl-2-oxo-6-(3-pyridinyl)-naphthalen-3-yl)carbonyl)glycine

HRID 1868641Notes

Reaction equation

[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[CH:10]=2)[C:5]([CH3:19])([CH3:18])[C:4](=[O:20])[C:3]=1[C:21]([NH:23][CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[O:22]>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[CH:10]=2)[C:5]([CH3:18])([CH3:19])[C:4](=[O:20])[C:3]=1[C:21]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:22]

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of 1,1-dimethylethyl N-((4-hydroxy-1,1-dimethyl-2-oxo-6-(pyridin-3-yl)-naphthalen-3-yl)carbonyl)glycinate (109 mg, 258 μmol) and silica gel (230-400 mesh, EMD Chemicals) (78 mg, 1290 μmol) in toluene (5 mL) was heated to 110° C. After 2 hours, the reaction was cooled to 23° C., filtered and washed with DCM (25 mL). The washings were discarded. The residue was subsequently washed with a 10% MeOH/DCM solution (1000 mL). The filtrate was then concentrated in vacuo affording 91 mg of the title compound. MS m/e=367.2 (M+H)+. Calculated for C20H18N2O5 366.12.

Workup

temperaturethe reaction was cooled to 23° C.
filtrationfiltered
washwashed with DCM (25 mL)
washThe residue was subsequently washed with a 10% MeOH/DCM solution (1000 mL)
concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record: ord-f46c7e1de99c4aac80094b8e91de5ad8
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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