Propanal → N-{(1S,2S)-1-[(2,4-Dimethyl-benzylamino)-methyl]-2-hydroxy-pentyl}-N'-(3-propylamino-5-trifluoromethyl-phenyl)-malonamide

A solution of {(2S,3S)-2-[2-(3-amino-5-trifluoromethyl-phenylcarbamoyl)-acetylamino]-3-hydroxyhexyl}-(2,4-dimethyl-benzyl)-carbamic acid benzyl ester (97 mg, 0.15 mmol) in MeOH (3 mL) was charged with propionaldehyde (0.01 mL, 0.15 mmol), stirred for 15 min at RT, and then charged with sodium cyanoborohydride (12 mg, 0.19 mmol). The reaction was stirred at RT for 12 h, concentrated in vacuo, and dissolved in EtOAc. The resultant solution was washed successively with water, sat. NaHCO3, water, and brine. The organic phase was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was dissolved in MeOH (3 mL). This solution was charged with 5% Pd/C, Degussa style (11 mg), stirred under H2 (1 atm) for 12 h at RT, filtered, and concentrated in vacuo. Purification of the residue by reverse-phase HPLC provided the title compound as a white powder after lyopholization. MS found: (M+H)+=537.4.

1. stirringThe reaction was stirred at RT for 12 h
2. concentrationconcentrated in vacuo
3. dissolutiondissolved in EtOAc
4. washThe resultant solution was washed successively with water, sat. NaHCO3, water, and brine
5. dry with materialThe organic phase was dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. dissolutionThe residue was dissolved in MeOH (3 mL)
9. additionThis solution was charged with 5% Pd/C, Degussa style (11 mg)
10. stirringstirred under H2 (1 atm) for 12 h at RT
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customPurification of the residue by reverse-phase HPLC

ORD record

ord-9681aa0ef279433b96d985ed3ea9229a

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07230133B2