(S)-6-(2-Methyl-allyl)-3-{(S)-1-[4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one → (S)-6-Isobutyl-3-{1-[4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one

HRID 473935Notes

Reaction equation

HRID 473935 reaction equation
[CH3:1][C:2](=[CH2:31])[CH2:3][C@:4]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:20][C:21]([CH3:24])=[N:22][N:23]=3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1>[Pd].O1CCCC1.[H][H]>[CH2:3]([C@:4]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:9][C:8](=[O:10])[N:7]([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:20][C:21]([CH3:24])=[N:22][N:23]=3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]([CH3:31])[CH3:1]

Participants

5

Reactant 1

HCID 66857751(S)-6-(2-Methyl-allyl)-3-{(S)-1-[4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one2×

Product 1

HCID 67997167(S)-6-Isobutyl-3-{1-[4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of (S)-6-(2-methyl-allyl)-3-{(S)-1-[4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one (48 mg; isomeric mixture from Intermediate X) and palladium on carbon (10 mg) in tetrahydrofuran (10 mL) was shaken in hydrogen atmosphere (50 psi) at room temperature for 6 h. Then, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (CH2Cl2/MeOH 99:1->95:5) to afford the title compound as a colorless resin-like solid.

Workup

  1. filtrationThen, the mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on silica gel (CH2Cl2/MeOH 99:1->95:5)

Sources & evidence

ORD record
ord-8df15c485a48436892c4340492b3de98
Source dataset
uspto-grants-2014_01
Patent number
US08637505B2

Reaction notes

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