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

HRID 1671459Notes

Reaction equation

HRID 1671459 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:33])([CH3:32])[C@@H:11]([O:22]CC1C=CC(OC)=CC=1)[C:12]([O:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:13])(=[O:7])=[O:6].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl.O>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:33])([CH3:32])[C@@H:11]([OH:22])[C:12]([O:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:13])(=[O:6])=[O:7]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86629051HCID 86629051, compound

Product 1

HCID 86629052HCID 86629052, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. customAfter work-up, the crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3b9509afd0ec44fba17c2dad36158436
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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