Bromoacetic Acid → HCID 20653463, compound

Participants

Reaction Steps

Bromoacetic acid (167 mg, 1.2 mmol) and diisopropylcarbodiimide (94 mm3, 0.6 mmol) were added to a suspension of the resin (4-(O-methylhydroxylamine)phenoxymethyl-copoly(styrene-1% divinylbenzene)-resin (100-200 mesh)) prepared according to Example 1 (250 mg, 0.1 mmol) in DMF (6 cm3). The mixture was agitated for 90 minutes and then the solution was drained from the resin which was washed and dried as described above in Example 1. The resin was soaked in DMSO (2 cm3) and a solution of n-decylamine in DMSO (5 cm5 of a 2 M solution. 10 mmol) was added and the mixture shaken for 4 h before the resin was drained and washed thoroughly as before. The resin was then suspended in DMF and 2-acetamido-4-methyl-5-thiazolesulfonylchloride (102 mg, 0.4 mmol) was added. The mixture was heated at 6° for 8 h and then the resin was drained, washed and dried as described previously. Cleavage from the resin as in Example A gave a white solid which was purified by column chromatography (10% methanol--dichloromethane; silica) to give the desired 2-(N-decyl-2-acetamido-4-methylthiazol-5-ylsulfonamido)-acetohydroxamic acid (23 mg, 51%) as a white solid; 1H NMR (CDCl3) δ3.83 (2 H, m), 3.05 (2 H, m), 2.52 (3 H, s, Me), 2.35 (3 H, s, NHCOMe), 1.69 (2 H, m), 1.15-1.25 (14 H, m, alkyl), 0.87 (3 H, t, J=7.2 Hz, CH3 -alkyl).

Provenance & Evidence