반응 #220150

반응 방정식

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

수율 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

수율 58.8%

용매

MeOH

반응 조건

후처리

1. 1
   여과The suspension was filtered over Celite
2. 2
   기타the product was purified by HPLC under standard conditions

실험 절차

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).

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