Diisopropylethylamine → tert-Butyl N-((5-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

HRID 2078244Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:20])=[C:5]([C:15](OCC)=[O:16])[C:6](=[O:14])[C:7]2([CH3:13])[CH3:12].Cl.[C:22]([O:26][C:27](=[O:30])[CH2:28][NH2:29])([CH3:25])([CH3:24])[CH3:23].CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:20])=[C:5]([C:15]([NH:29][CH2:28][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:30])=[O:16])[C:6](=[O:14])[C:7]2([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 75 °C

Procedure

Ethyl 5-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (210 mg, 713 μmol, 1.0 eq) and glycine tert-butyl ester hydrochloride (143 mg, 855 μmol, 1.20 eq) were mixed in dioxane (5 mL) in a round bottom flask. DIPEA (186 μL, 1069 μmol, 1.5 eq) was added via syringe, and the reaction was stirred at 75° C. for 4 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo to give a yellow solid. The crude product was purified by silica flash chromatography (0-50% DCM/hexane) to give the desired compound as a white solid (204 mg). MS m/e=380 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
customto give a yellow solid
customThe crude product was purified by silica flash chromatography (0-50% DCM/hexane)

Sources & evidence

ORD record: ord-1be9ab0a37954eb89c1d79af96ccec78
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928139B2

Reaction notes

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