Water → HCID 67099740, compound

HRID 2078119Notes

Reaction equation

[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12][CH3:13])[CH:10]=2)[C:5]([CH3:15])([CH3:14])[C:4](=[O:16])[C:3]=1[C:17](OCC)=[O:18].Cl.[C:23]([O:27][C:28](=[O:31])[CH2:29][NH2:30])([CH3:26])([CH3:25])[CH3:24].CCN(C(C)C)C(C)C.O>O1CCOCC1>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12][CH3:13])[CH:10]=2)[C:5]([CH3:14])([CH3:15])[C:4](=[O:16])[C:3]=1[C:17]([NH:30][CH2:29][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:31])=[O:18]

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of ethyl 4-hydroxy-1,1-dimethyl-6-(methylthio)-2-oxo-naphthalen-3-carboxylate (0.800 g, 2.61 mmol), glycine tert-butyl ester hydrochloride (0.525 g, 3.13 mmol) and DIPEA (0.910 mL, 5.22 mmol in 1,4-dioxane (25 mL) in a 75 mL sealed vessel, was stirred at 120° C. for 3 hours. Deionized water (75 mL) was added, and the resulting mixture was extracted with EtOAc (2×50 mL). The combined organic layers were then washed with brine (50 mL). The organic layer was dried over MgSO4, concentrated, and dried in vacuo to give 1.44 g crude product which was purified by flash column chromatography (silica, 0-50% DCM in hexane) to give the title compound (0.886 g). MS m/e=336 (M+H-tBu)+.

Workup

extractionthe resulting mixture was extracted with EtOAc (2×50 mL)
washThe combined organic layers were then washed with brine (50 mL)
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated
customdried in vacuo
customto give 1.44 g crude product which
customwas purified by flash column chromatography (silica, 0-50% DCM in hexane)

Sources & evidence

ORD record: ord-815af5d942b948bca9a79984c2a29c94
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928139B2

Reaction notes

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