2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86695113, compound

HRID 1503938Notes

Reaction equation

COC1C=CC(CO[CH2:11][CH2:12][O:13][CH2:14][C@H:15]2[CH2:26][CH2:25][C:24]3[S:23][C:22]4[N:21]=[CH:20][N:19]=[C:18]([O:27][CH:28]5[CH2:33][CH2:32][CH:31]([N:34]([CH3:42])[C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:30][CH2:29]5)[C:17]=4[C:16]2=3)=CC=1.C(C1C(=O)C(Cl)=C(Cl)[C:47](=[O:48])C=1C#N)#N>ClCCl.O>[OH:48][CH2:47][CH2:11][CH2:12][O:13][CH2:14][C@H:15]1[CH2:26][CH2:25][C:24]2[S:23][C:22]3[N:21]=[CH:20][N:19]=[C:18]([O:27][CH:28]4[CH2:29][CH2:30][CH:31]([N:34]([CH3:42])[C:35](=[O:41])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40])[CH2:32][CH2:33]4)[C:17]=3[C:16]1=2

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of tert-butyl N-(4-[[(3S)-3-([2-[(4-methoxyphenyl)methoxy]ethoxy]methyl)-7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (700 mg, 1.17 mmol, 1.00 equiv) in dichloromethane (10 mL)/water (0.5 mL) was added DDQ (399 mg, 1.76 mmol, 1.50 equiv) and the resulting solution was stirred for 14 hrs at 25° C. under nitrogen. The resulting solution was diluted with water and extracted with 3×100 mL of ethyl acetate. The organic layers were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1) to give tert-butyl N-(4-[[(3S)-3-[(3-hydroxypropoxy)methyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (370 mg, 64%) as a colorless oil. MS: m/z 478 (M+H)+.

Workup

extractionextracted with 3×100 mL of ethyl acetate
washwashed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-447cc346954a4fdabaa702800075c90f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

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