HCID 68508740, compound → HCID 59997883, compound

from benzyl methyl-6-[(1R,3S)-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)-cyclohexyloxymethyl]benzoate: 15 g (27.8 mmol) of benzyl methyl-6-[(1R,3S)-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyloxymethyl]benzoate are dissolved in 300 ml of THF. 700 mg of palladium on carbon (5%) are added. Subsequently, hydrogenation is effected at standard pressure and RT until no more hydrogen is taken up. The reaction mixture is filtered and the organic phase is subsequently concentrated fully under reduced pressure. The residue is taken up in 150 ml of tert-butyl methyl ether, 150 ml of water and 150 ml of saturated sodium hydrogencarbonate solution. After phase separation, the aqueous phase is washed with 150 ml of tert-butyl methyl ether. Subsequently, 150 ml of diisopropyl ether are added and the mixture is acidified with concentrated hydrochloric acid. After phase separation, the organic phase is washed four times with 100 ml each time of water and then concentrated fully under reduced pressure. The residue is stirred with a little diisopropyl ether. The solid is filtered and dried under reduced pressure. 2-methyl-6-[(1R,3S)-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl-oxymethyl]benzoic acid is obtained in 42% yield as a crystalline solid.

1. filtrationThe reaction mixture is filtered
2. concentrationthe organic phase is subsequently concentrated fully under reduced pressure
3. customAfter phase separation
4. washthe aqueous phase is washed with 150 ml of tert-butyl methyl ether
5. additionSubsequently, 150 ml of diisopropyl ether are added
6. customAfter phase separation
7. washthe organic phase is washed four times with 100 ml each time of water
8. concentrationconcentrated fully under reduced pressure
9. filtrationThe solid is filtered
10. customdried under reduced pressure

ORD record

ord-c71b1bb7652f4e86a017a8c78bb5ec4a

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803950B2