HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzoyl Peroxide → N1-[(1S,3S,4S)-4-{[(2S)-2-(3-benzyl-2-oxoimidazolidin-1-yl)-3,3-dimethylbutanoyl]amino}-3-[1-(ethylthio)ethoxy]-5-phenyl-1-(4-pyridin-2-ylbenzyl)pentyl]-N2-(methoxycarbonyl)-3-methyl-L-valinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoyl Peroxide | HCID 7187 | — |
| Reactant | Ethyl sulfide | HCID 9609 | — |
| Reactant | A-792611 | HCID 11274374 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | N1-[(1S,3S,4S)-4-{[(2S)-2-(3-benzyl-2-oxoimidazolidin-1-yl)-3,3-dimethylbutanoyl]amino}-3-[1-(ethylthio)ethoxy]-5-phenyl-1-(4-pyridin-2-ylbenzyl)pentyl]-N2-(methoxycarbonyl)-3-methyl-L-valinamide | HCID 67406314 | 95% |
Reaction Steps
To a solution of the compound of Example 111 (0.200 g, 0.248 mmol) and ethyl sulfide (0.70 mL, 6.48 mmol) in acetonitrile (2.0 mL) at 0° C. was added benzoyl peroxide (0.38 g, 1.57 mmol) in three portions over 2 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 starting with dichloromethane and ending with ethyl acetate to give the title compound (0.210 g, 95% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07834043B2 |
| Source dataset | uspto-grants-2010_11 |
| ORD ID | ord-0ddf5f90162c4aee986ed29066d0ae96 |
| Source note | uspto-grants-2010_11 |