Reacción #220150

Ecuación de reacción

hydrogen

( B )

(S)-2-((S)-3-acetamido-3-((R)-sec-butyl)-2-oxopyrrolidin-1-yl)-N-((1S,2S)-1-((2R,4R)-1-benzhydryl-4-hydroxypyrrolidin-2-yl)-3-(3,5-difluorophenyl)-1-hydroxypropan-2-yl)-4-phenylbutanamide

compound

(S)-2-((S)-3-acetamido-3-((R)-sec-butyl)-2-oxopyrrolidin-1-yl)-N-((1S,2S)-1-((R)-1-benzhydrylpiperidin-2-yl)-3-(3,5-difluorophenyl)-1-hydroxypropan-2-yl)-4-phenylbutanamide

acetic acid

→

title compound

Rendimiento 58.8%

(S)-2-((S)-3-acetamido-3-((R)-sec-butyl)-2-oxopyrrolidin-1-yl)-N-((1S,2S)-3-(3,5-difluorophenyl)-1-hydroxy-1-((R)-morpholin-3-yl)propan-2-yl)-4-phenylbutanamide

Rendimiento 58.8%

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe suspension was filtered over Celite
2. 2
   Otrothe product was purified by HPLC under standard conditions

Procedimiento

Step 16 (B): To 20 mg of 10% Pd/C was added a solution of the entire sample of the compound of step 16 (A) in 5 ml of MeOH under nitrogen. A 0.3 ml portion of acetic acid was added. The mixture was shaken in a Parr apparatus with 50 psi of hydrogen for 3.5 hours. The suspension was filtered over Celite, and the product was purified by HPLC under standard conditions to give 30 mg (58.8% yield for the two steps) of the title compound of Example 16. 1H NMR (500 MHz, CDCl3) δ ppm 0.90 (d, J=6.71 Hz, 3 H) 1.02 (t, J=7.17 Hz, 3 H) 1.13 (m, 1 H) 1.72 (m, 2 H) 2.00 (s, 3 H) 2.12 (m, 1 H) 2.21 (q, J=7.12 Hz, 2 H) 2.38 (m, 1 H) 2.57 (m, 1 H) 2.74 (m, 2 H) 3.23 (dd, J=14.34, 2.75 Hz, 1 H) 3.31 (m, 5 H) 3.42 (m, 2 H) 3.70 (m, 1 H) 3.77 (m, 1 H) 3.91 (m, 2 H) 3.99 (m, 2 H) 4.21 (dd, J=12.51, 3.05 Hz, 1 H) 6.73 (tt, J=9.16, 2.14 Hz, 1 H) 6.87 (d, J=7.94 Hz, 2 H) 7.19 (d, J=5.80 Hz, 3 H) 7.27 (m, 2 H) 8.12 (s, 1 H) 8.25 (d, J=8.85 Hz, 1 H).

Fuente