HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoyl Peroxide | HCID 7187 | — |
| Reactant | Ethyl sulfide | HCID 9609 | — |
| Reactant | Lopinavir | HCID 92727 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (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 | HCID 42637794 | 61% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08426388B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-6db99bc07bc646aeac3fdba2ba0967a3 |
| Source note | uspto-grants-2013_04 |