2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86730727, compound

HRID 633853Notes

Reaction equation

HRID 633853 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[C:15]([O:19][C:20]([NH:22][C@H:23]1[CH2:28][O:27][CH:26]([CH2:29][C@@H:30]2[O:45][C:33]3[CH:34]=[N:35][C:36]4[CH:37]=[CH:38][C:39]([O:43][CH3:44])=[C:40]([F:42])[C:41]=4[C:32]=3[CH:31]2OC(=O)C)[CH2:25][CH2:24]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[C:15]([O:19][C:20](=[O:21])[NH:22][C@@H:23]1[CH2:24][CH2:25][C@@H:26]([CH2:29][CH:30]2[O:45][C:33]3[CH:34]=[N:35][C:36]4[CH:37]=[CH:38][C:39]([O:43][CH3:44])=[C:40]([F:42])[C:41]=4[C:32]=3[CH2:31]2)[O:27][CH2:28]1)([CH3:16])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8058HexaneHCID 8857Ethyl AcetateHCID 86730726HCID 86730726, compound

Product 1

HCID 86730727HCID 86730727, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (833 mg, 3.67 mmol, 5.0 eq) is added at room temperature to a stirred solution of acetic acid 2-(2S,5R)-(5-tert-butoxycarbonylamino-tetrahydro-pyran-2-ylmethyl)-9-fluoro-8-methoxy-1,2-dihydro-furo[2,3-c]quinolin-1-yl ester (360 mg, 0.73 mmol, 1.0 eq) in toluene (60 mL). After 2 hours stirring at room temperature, solvent is evaporated and the residue is extracted with dichloromethane (3×100 mL) and a saturated sodium carbonate aqueous solution (100 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: n-hexane:ethyl acetate, 10:1 to 1:1, v/v) to afford (3R,6S)-[6-(9-fluoro-8-methoxy-1,2-dihydro-furo[2,3-c]quinolin-2-ylmethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester as a light yellow solid (75 mg, 24% yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with dichloromethane (3×100 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product that
  7. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-d6d6795ab9334965812e1c78a186c996
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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