Formaldehyde → N-{(1S,2S)-1-[(2,4-Dimethyl-benzylamino)-methyl]-2-hydroxy-pentyl}-N'-(3-methylamino-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 (83 mg, 0.13 mmol, see procedure 12c) in 1,2-dichloroethane (2 mL) was charged with formaldehyde (0.008 mL of a 37% aq. solution, 0.10 mmol), stirred for 20 min at RT, and then charged with sodium triacetoxyborohydride (69 mg, 0.33 mmol). The reaction was stirred at RT for 40 min, quenched with water, and extracted with EtOAc (2×). The organic extracts were washed with water and brine, and then dried (Na2SO4), filtered, and concentrated in vacuo. The residue was dissolved in MeOH (2 mL). This solution was charged with 5% Pd/C, Degussa style (7 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)+=509.3.

1. stirringThe reaction was stirred at RT for 40 min
2. customquenched with water
3. extractionextracted with EtOAc (2×)
4. washThe organic extracts were washed with water and brine
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. dissolutionThe residue was dissolved in MeOH (2 mL)
9. additionThis solution was charged with 5% Pd/C, Degussa style (7 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レコード

ord-15f607a7621c4351b746d9cf9775e90f

出典データセット

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07468440B2