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

Participants

Role	Name	HCID	Charge
Reactant	Dimethyl Sulfide	HCID 1068	—
Reactant	Benzoyl Peroxide	HCID 7187	—
Reactant	methyl 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	HCID 56594083	—
Solvent	Acetonitrile	HCID 6342	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	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	HCID 86726256	77%

Reaction Conditions

Temperature	0 °C

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07834043B2
Source dataset	uspto-grants-2010_11
ORD ID	ord-1ec19210359a4d8cbff39f53d3b6097b
Source note	uspto-grants-2010_11