Benzoyl Peroxide → (2s)-n-{(1s,3s,4s)-1-Benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-[1-(ethylthio)ethoxy]-5-phenylpentyl}-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanamide

HRID 1968906Notes

Reaction equation

HRID 1968906 reaction equation
[CH2:1]([C@H:8]([NH:33][C:34](=[O:46])[C@@H:35]([N:39]1[CH2:44][CH2:43][CH2:42][NH:41][C:40]1=[O:45])[CH:36]([CH3:38])[CH3:37])[CH2:9][C@H:10]([OH:32])[C@@H:11]([NH:19][C:20](=[O:31])[CH2:21][O:22][C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:30])[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.[CH2:47]([S:49][CH2:50][CH3:51])[CH3:48].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:33][C:34](=[O:46])[C@@H:35]([N:39]1[CH2:44][CH2:43][CH2:42][NH:41][C:40]1=[O:45])[CH:36]([CH3:38])[CH3:37])[CH2:9][C@H:10]([O:32][CH:47]([S:49][CH2:50][CH3:51])[CH3:48])[C@@H:11]([NH:19][C:20](=[O:31])[CH2:21][O:22][C:23]1[C:24]([CH3:30])=[CH:25][CH:26]=[CH:27][C:28]=1[CH3:29])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 9609Ethyl sulfideHCID 92727Lopinavir

Product 1

HCID 42637794(2s)-n-{(1s,3s,4s)-1-Benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-[1-(ethylthio)ethoxy]-5-phenylpentyl}-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanamideYield 61%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound of Example 3 (0.50 g, 0.80 mmol) and ethyl sulfide (2.1 mL) in acetonitrile (6 mL) at 0° C. was added benzoyl peroxide (1.16 g) in three portions over 3 hours. The reaction was diluted with ethyl acetate and washed with 10% Na2CO3 and brine. The organic was dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel eluting with a gradient of 50-100% ethyl acetate in chloroform to give the title compound (0.36 g, 61% yield).

Workup

  1. washwashed with 10% Na2CO3 and brine
  2. dry with materialThe organic was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was chromatographed on silica gel eluting with a gradient of 50-100% ethyl acetate in chloroform

Sources & evidence

ORD record
ord-6db99bc07bc646aeac3fdba2ba0967a3
Source dataset
uspto-grants-2013_04
Patent number
US08426388B2

Reaction notes

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