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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1174248Generated: October 31, 2026

Lithium Chloride → benzyl(4S,5S)-5-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}-2,2-dimethyl-4-[4-(4-methyl-2-pyridinyl)benzyl]-1,3-oxazolidine-3-carboxylate

https://huagongshe.com/reaction/1174248

Reaction equation

Participants

RoleNameHCIDCharge
ReactantLithium ChlorideHCID 433294—
Reactant4-Methyl-2-(tributylstannyl)pyridineHCID 11222775—
Reactantbenzyl(4S,5S)-5-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}-2,2-dimethyl-4-{4-[(trifluoroacetyl)oxy]benzyl}-1,3-oxazolidine-3-carboxylateHCID 67407042—
CatalystHCID 178418476HCID 178418476—
SolventDimethylformamideHCID 6228—
Productbenzyl(4S,5S)-5-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}-2,2-dimethyl-4-[4-(4-methyl-2-pyridinyl)benzyl]-1,3-oxazolidine-3-carboxylateHCID 6740689239%

Reaction Steps

A solution containing the product from Example 23I (0.183 g, 0.259 mmol) in DMF (2.6 mL) was treated with LiCl (0.110 g, 2.59 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.055 g, 0.078 mmol), and the product from Example 80A (0.495 g, 1.29 mmol), heated at 100° C. for 16 hours, cooled and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-10% ethyl acetate in dichloromethane, to give the title compound (0.065 g, 39% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07834043B2
Source datasetuspto-grants-2010_11
ORD IDord-9e45e85813854676b9665e2940022baf
Source noteuspto-grants-2010_11