2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86629052, compound

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Reaction Steps

Following the general procedure for the oxidative cleavage of (4-methoxy)benzyl ethers of Description 19, 3-pyridylmethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-2-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutanoate (37a) (0.30 g, 0.60 mmol) dissolved in a mixture of dichloromethane (DCM) and water (10:1) (5 mL) was treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (190 mg, 0.84 mmol). After work-up, the crude material was purified by silica gel column chromatography using ethyl acetate (EtOAc) to provide 20 mg (9% yield) of the title compound (37b) as a white solid. 1H NMR (400 MHz, CDCl3): δ=0.96 (s, 3H), 1.08 (s, 3H), 2.29-2.36 (m, 2H), 3.28-3.32 (m, 2H), 3.67-3.70 (m, 2H), 3.98 (d, J=9.2 Hz, 1H), 4.08 (s, 1H), 4.15 (d, J=9.2 Hz, 1H), 5.20 (s, 2H), 7.32-7.35 (m, 1H), 7.72-7.75 (m, 1H), 8.60-8.65 (m, 2H) ppm. MS (ESI) m/z: 379.99 (M+H)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence