Dimethyl Sulfide → methyl (1S)-1-({[(1S,3S,4S)-1-benzyl-4-{[N-(methoxycarbonyl)-3-methyl-L-valyl]amino}-3-[(methylthio)methoxy]-5-(4-pyridin-2-ylphenyl)pentyl]amino}carbonyl)-2,2-dimethylpropylcarbamate

HRID 1174416Notes

Reaction equation

HRID 1174416 reaction equation
[CH3:1][O:2][C:3](=[O:51])[NH:4][C@@H:5]([C:47]([CH3:50])([CH3:49])[CH3:48])[C:6](=[O:46])[NH:7][C@@H:8]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=2)=[CH:36][CH:35]=1)[C@@H:9]([OH:32])[CH2:10][C@H:11]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:12][C:13](=[O:24])[C@H:14]([C:20]([CH3:23])([CH3:22])[CH3:21])[NH:15][C:16](=[O:19])[O:17][CH3:18].[CH3:52][S:53][CH3:54].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(#N)C.C(OCC)(=O)C>[CH2:25]([C@H:11]([NH:12][C:13]([C@@H:14]([NH:15][C:16](=[O:19])[O:17][CH3:18])[C:20]([CH3:23])([CH3:22])[CH3:21])=[O:24])[CH2:10][C@H:9]([O:32][CH2:52][S:53][CH3:54])[C@@H:8]([NH:7][C:6](=[O:46])[C@H:5]([C:47]([CH3:50])([CH3:49])[CH3:48])[NH:4][C:3]([O:2][CH3:1])=[O:51])[CH2:33][C:34]1[CH:35]=[CH:36][C:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=2)=[CH:38][CH:39]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 7187Benzoyl PeroxideHCID 56594083methyl N-[(1S)-1-[[(1S,3S,4S)-1-benzyl-3-hydroxy-4-[[(2S)-2-(methoxycarbonylamino)-3,3-dimethyl-butanoyl]amino]-5-[4-(2-pyridyl)phenyl]pentyl]carbamoyl]-2,2-dimethyl-propyl]carbamate

Product 1

HCID 86726256methyl (1S)-1-({[(1S,3S,4S)-1-benzyl-4-{[N-(methoxycarbonyl)-3-methyl-L-valyl]amino}-3-[(methylthio)methoxy]-5-(4-pyridin-2-ylphenyl)pentyl]amino}carbonyl)-2,2-dimethylpropylcarbamateYield 77%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the compound of Example 25 (0.125 g, 0.178 mmol) and methyl sulfide (0.405 mL, 5.48 mmol) in acetonitrile (0.75 mL) at 0° C. was added benzoyl peroxide (0.63 g, 2.60 mmol), and the mixture was stirred at 0° C. for 1 hour. 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 (0.104 g, 77% 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

Sources & evidence

ORD record
ord-1ec19210359a4d8cbff39f53d3b6097b
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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