1,4-Dioxane → HCID 67099704, compound

HRID 1868857Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of ethyl 8-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (0.320 g, 0.803 mmol), glycine tert-butyl ester hydrochloride (0.175 g, 1.04 mmol), DIEA (0.280 mL, 1.61 mmol), and 1,4-dioxane (12 mL) were heated at 120° C. for 2 hours in a sealed vessel. The mixture was diluted with water (50 mL) and extracted with DCM (2×50 mL). The combined organic layers were washed with water (30 mL) and then with brine (50 mL), dried over MgSO4, and concentrated and dried in vacuo. The residue was purified by flash column chromatography (silica, 0-50% DCM in hexane) to give 1,1-dimethylethyl N-((8-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (0.214 g). MS m/e=378 (M−H)−.

Workup

extractionextracted with DCM (2×50 mL)
washThe combined organic layers were washed with water (30 mL)
dry with materialwith brine (50 mL), dried over MgSO4
concentrationconcentrated
customdried in vacuo
customThe residue was purified by flash column chromatography (silica, 0-50% DCM in hexane)

Sources & evidence

ORD record: ord-e810e8bbd9114be38bdbe6dabaa36e27
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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