Hydrogen Peroxide → (2S,3R)-5-(3',5'-difluorobiphenyl-4-yl)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-(formyloxy)pentanoic acid

HRID 1892150Notes

Reaction equation

[CH:1]([O:3][C@H:4]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[C:33]([F:35])[CH:32]=[C:31]([F:36])[CH:30]=2)=[CH:25][CH:24]=1)[C@@H:5]([CH:19]=[O:20])[CH2:6][CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])=[O:2].P([O-])(O)(O)=[O:38].[Na+].OO.Cl([O-])=O.[Na+]>C(#N)C.O>[F:35][C:33]1[CH:34]=[C:29]([C:26]2[CH:25]=[CH:24][C:23]([CH2:22][CH2:21][C@@H:4]([O:3][CH:1]=[O:2])[C@H:5]([CH2:6][CH2:7][N:8]3[C:9](=[O:18])[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:16]3=[O:17])[C:19]([OH:38])=[O:20])=[CH:28][CH:27]=2)[CH:30]=[C:31]([F:36])[CH:32]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The compound (0.12 g) obtained from step d was taken in acetonitrile (6 mL) and water (1 mL), to this solution sodiumdihydrogen phosphate (0.05 g) was added. Reaction mixture was cooled to 0° C. and hydrogen peroxide (0.5 mL) and sodium chlorite (0.15 g) were added. After stirring the reaction mixture for additional 1 hour, solvents were evaporated on rotaevaporator, the residue was taken into water and extracted with ethyl acetate. Organic layer was washed with water and brine solution and dried over anhydrous sodium sulphate. Solvent was evaporated under the reduced pressure, to get the title compound (0.12 g)

Workup

customReaction mixture
customsolvents were evaporated on rotaevaporator
extractionextracted with ethyl acetate
washOrganic layer was washed with water and brine solution
dry with materialdried over anhydrous sodium sulphate
customSolvent was evaporated under the reduced pressure

Sources & evidence

ORD record: ord-6e380f31c8994a0fab80f5f2f21c2ed6
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507670B2

Reaction notes

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