Diethylethanolamine → (s)-2-((s)-3-Acetamido-3-((r)-sec-butyl)-2-oxopyrrolidin-1-yl)-n-((1r,2s)-1-hydroxy-3-phenyl-1-((2r,4r)-4-(propylsulfonyl)pyrrolidin-2-yl)propan-2-yl)-4-phenylbutanamide

Participants

Reaction Steps

Step 22 (F): (2R,4R)-tert-butyl 2-((1S,2S)-2-((S)-2-((S)-3-acetamido-3-((R)-sec-butyl)-2-oxopyrrolidin-1-yl)-4-phenylbutanamido)-1-(tert-butyldimethylsilyloxy)-3-phenylpropyl)-4-(propylsulfonyl)pyrrolidine-1-carboxylate. A solution of the compound of Preparation A (22 mg, 0.06 mmol) dissolved in 2 mL of dichloromethane was treated with DEEA (40 mg, 0.3 mmol) and HATU (30 mg, 0.078 mmol). After stirring at rt for 5 min, the amine from step 22 (E) (32 mg, 0.06 mmol) was added and the reaction solution was allowed to stir for 16 h at rt. The reaction solution was then partitioned between ethyl acetate and water, the organic layer was concentrated, and the crude product was purified by chromatography eluting with a gradient of 40% to 80% ethyl acetate in hexanes to provide 45 mg (85%) of the desired amide. 1H NMR (500 MHz, Solvent) δ ppm 0.08 (s, 6 H) 0.18 (s, 2 H) 0.73 (d, J=6.71 Hz, 3 H) 0.99 (s, 9 H) 1.10 (m, 6 H) 1.37 (t, J=6.41 Hz, 6 H) 1.49 (s, 9 H) 1.52 (d, J=3.97 Hz, 4 H) 1.68 (m, 1 H) 1.86 (m, 2 H) 2.09 (m, 1 H) 2.58 (m, 1 H) 2.73 (m, 1 H) 3.05 (dd, J=9.16, 6.41 Hz, 2 H) 3.23 (m, 2 H) 3.54 (s, 1 H) 3.76 (m, 2 H) 4.02 (m, 2 H) 4.09 (m, 1 H) 4.26 (s, 1 H) 4.41 (d, J=8.55 Hz, 1 H) 7.22 (m, 10 H) 8.18 (s, 1 H). MS (ESI) (M+H)+=883.41

Provenance & Evidence