Diisopropylethylamine → HCID 67099310, compound

HRID 1868720Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of crude ethyl 6-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-carboxylate (4100 mg, 12088 μmol) and glycine tert-butyl ester hydrochloride (2229 mg, 13297 μmol) in 1,4-dioxane (100 mL) was treated with DIPEA (4211 μL, 24176 μmol). The reaction was heated at 120° C. in a sealed vessel. After 17 hours, the reaction was cooled to 23° C., diluted with EtOAc (200 mL) and washed with 10% HCl solution (2×150 mL) and brine (100 mL). The organic layer was dried over MgSO4, concentrated in vacuo, and purified by silica gel chromatography (eluant: 5-10% EtOAc/hexane) affording 2523 mg of 1,1-dimethylethyl N-((6-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate. MS m/e=422.0 (M−H)−.

Workup

temperaturethe reaction was cooled to 23° C.
washwashed with 10% HCl solution (2×150 mL) and brine (100 mL)
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo
custompurified by silica gel chromatography (eluant: 5-10% EtOAc/hexane)

Sources & evidence

ORD record: ord-03c3d27fb3b9407ab21ad5ce0357c9f0
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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