Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 66785824, compound

Participants

Reaction Steps

(R)-1-(3-methoxypropyl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole (138C) (3.02 g) was coupled to (3R,4S)-4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (5 g) (138B) using the standard BOP coupling procedure from Example 138, Step C, Procedure B. The deprotection was performed according to standard procedures (TFA/CH2Cl2; evapn; EtOAc/satd NaHCO3; dry; evapn.) to yield the free amine, (9H-fluoren-9-yl)methyl (3S,4R)-4-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carbonyl)pyrrolidin-3-ylcarbamate (139E): ESI-MS: m/z 608.6 (MH+). 1H NMR (400 MHz, MeOH-d4) δ ppm 1.66 (m, 1H) 1.7-2.3 (m, 5H) 4.21-4.25 (m, 2H) 7.1-7.6 (m, 8H). HPLC retention time, T=0.817 min, STDTFA-2 method.

Provenance & Evidence