Pyridine → 3-benzyloxy-4-[(S)-2-tert-butoxycarbonyl-1-(methoxy-methyl-carbamoyl)-ethylsulfamoyl]-benzoic acid methyl ester

Participants

Reaction Steps

To a solution of 3-benzyloxy-4-chlorosulfonyl-benzoic acid methyl ester (9.25 g, 27.1 mmol) in dichloromethane (270 mL) was added (S)-3-amino-N-methoxy-N-methyl-succinamic acid tert-butyl ester (6.30 g, 27.1 mmol) followed by pyridine (6.59 mL, 81.4 mmol). The reaction was allowed to stir over night at room temperature. The reaction was then diluted with ethyl acetate (500 mL) and washed sequentially with 5% citric acid, saturated sodium bicarbonate, and saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield an orange oil. The crude residue was chromatographed (silica gel, 40% ethyl acetate-60% hexane) to give 3-benzyloxy-4-[(S)-2-tert-butoxycarbonyl-1-(methoxy-methyl-carbamoyl)-ethylsulfamoyl]-benzoic acid methyl ester as a white foam (8.20 g, 56%). 1H NMR(300 MHz, DMSO) 7.84 (d, 1H), 7.60 (m, 1H), 7.57 (m, 2H), 7.52 (d, 2H), 7.36 (t, 2H), 7.28 (t, 1H), 5.35 (s, 2H), 4.60 (m, 1H), 3.81 (s, 3H), 3.48 (bs, 3H), 2.82 (bs, 3H), 2.46 (dd, 1H), 2.33 (dd, 1H), 1.27 (s, 9H). MS(APCI) m/z 535.2 (M−H).

Provenance & Evidence