Sodium Carbonate → [3'-(5-Carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-6-methyl-biphenylylmethoxy]-acetic acid trifluoroacetate

Participants

Reaction Steps

The procedure used in Example 1: step c was followed using {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 27: step c) (239 mg, 0.24 mmol)), [4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyloxy]-acetic acid tert-butyl ester ((Example 300: step c) 530 mg, 1.46 mmol), Na2CO3 (2M, 3 mL, 6 mmol), Pd(PPh3)4 (70 mg, 0.06 mmol), ethanol (3 mL) and toluene (6 mL). Analogous aqueous workup yielded 629 mg of crude material which was treated with 1:1 TFA/DCM as described in Example 1: step d. Analogous purification by C18-HPLC yielded the title compound (47 mg, 38%) as a white solid. RP-HPLC (5 to 100% ACN over 8 min) analytical purity=100%. ESI-MS (m/z): Calcd. for C22H22N2O5S3 (M+H): 491.1; found: 491.1.

Provenance & Evidence