Benzoyl Peroxide → HCID 42637793, compound

HRID 1968920Notes

Reaction equation

HRID 1968920 reaction equation
[CH2:1]([C@H:8]([NH:30][C:31](=[O:50])[C@H:32]([CH:47]([CH3:49])[CH3:48])[NH:33][C:34]([N:36]([CH2:38][C:39]1[N:40]=[C:41]([CH:44]([CH3:46])[CH3:45])[S:42][CH:43]=1)[CH3:37])=[O:35])[CH2:9][C@H:10]([OH:29])[C@@H:11]([NH:19][C:20]([O:22][CH2:23][C:24]1[S:28][CH:27]=[N:26][CH:25]=1)=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:51]([S:55][CH2:56][CH:57]([CH3:59])[CH3:58])[CH:52]([CH3:54])[CH3:53].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(#N)C.C(OCC)(=O)C>[CH2:1]([C@H:8]([NH:30][C:31](=[O:50])[C@H:32]([CH:47]([CH3:49])[CH3:48])[NH:33][C:34]([N:36]([CH2:38][C:39]1[N:40]=[C:41]([CH:44]([CH3:45])[CH3:46])[S:42][CH:43]=1)[CH3:37])=[O:35])[CH2:9][C@H:10]([O:29][CH:51]([S:55][CH2:56][CH:57]([CH3:59])[CH3:58])[CH:52]([CH3:54])[CH3:53])[C@@H:11]([NH:19][C:20]([O:22][CH2:23][C:24]1[S:28][CH:27]=[N:26][CH:25]=1)=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 11608Propane, 1,1'-thiobis[2-methyl-HCID 392622Ritonavir

Product 1

HCID 42637793HCID 42637793, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the compound of Example 1 (1.0 g, 1.38 mmol) and diisobutyl sulfide (6.2 mL) in acetonitrile (10 mL) at 0° C. was added benzoyl peroxide (2.0 g) in three portions over 30 minutes, and the reaction was stirred at 0° C. for 1 hour. The reaction was diluted with ethyl acetate and washed with 10% Na2CO3 and brine. The organic phase was dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel eluting with a gradient starting with 0-100% ethyl acetate/dichloromethane to provide the title product (0.890 g, 75% yield).

Workup

  1. washwashed with 10% Na2CO3 and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was chromatographed on silica gel eluting with a gradient

Sources & evidence

ORD record
ord-5991e77c2f204c09b71c7c44a2702fcf
Source dataset
uspto-grants-2013_04
Patent number
US08426388B2

Reaction notes

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