2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 58573923, compound

HRID 932265Notes

Reaction equation

HRID 932265 reaction equation
[CH2:1]([C@:4]1([CH2:37][CH2:38][O:39]CC2C=CC(OC)=CC=2)[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:34][CH3:35])[CH2:25][N:26]([CH3:33])[S:27]([CH:30]2[CH2:32][CH2:31]2)(=[O:29])=[O:28])[C:5]1=[O:36])[CH:2]=[CH2:3].C(C1C=CC=C(C(C)(C)C)N=1)(C)(C)C.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl.O.C([O-])(O)=O.[Na+].[Cl-].[Na+].O>[CH2:1]([C@:4]1([CH2:37][CH2:38][OH:39])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:34][CH3:35])[CH2:25][N:26]([CH3:33])[S:27]([CH:30]2[CH2:32][CH2:31]2)(=[O:28])=[O:29])[C:5]1=[O:36])[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 685102,6-Di-tert-butylpyridineHCID 67999073HCID 67999073, compound

Product 1

HCID 58573923HCID 58573923, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 129703874Sodium hydrogencarbonate brineSolvent

Procedure

To a solution of 3.09 g (4.33 mmol) N-((S)-2-((3R,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-(2-(4-methoxybenzyloxy)ethyl)-2-oxopiperidin-1-yl)butyl)-N-methylcyclopropanesulfonamide (Example 408, step C) in a mixture of DCM (82 mL) and water (4.56 mL) [18:1] was added 2,6-di-tert-butylpyridine (2.93 mL, 12.99 mmol) followed by DDQ (3.93 g, 17.32 mmol). The reaction mixture was stirred vigorously at ambient temperature for 15 min. The reaction mixture was diluted with 150 mL sat. NaHCO3/brine solution and extracted into 600 mL of ethyl acetate, then 200 mL of EtOAc×2 (precipitate was removed by filtration). The combined organic layers were dried over MgSO4, filtered and the filtrate was evaporated. Purification by chromatography on silica gel (eluent: 50-100%% EtOAc/hexane, gradient elution) provided the desired product as a foam.

Workup

  1. extractionextracted into 600 mL of ethyl acetate
  2. custom200 mL of EtOAc×2 (precipitate was removed by filtration)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customthe filtrate was evaporated
  6. customPurification by chromatography on silica gel (eluent: 50-100%% EtOAc/hexane, gradient elution)

Sources & evidence

ORD record
ord-739ed58ef3894838944887bfaa76bfb0
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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