Hydrochloric Acid → HCID 20334542, compound

Participants

Reaction Steps

A slurry of 3-(γ-oxo-δ-acetoxybutylamino)-4-phenoxy-5-sulfamylbenzoic acid (1.5 g) in ethanol (10 ml) was treated with sodium borohydride (0.5 g) and the mixture was heated on the steam bath with occasional swirling until a clear solution had formed. Water and aq. Na2CO3 were added and heating on the steam bath continued for about 10 min. The solution was cooled and carefully acidified with 3 N aqueous HCl. Some methanol was added and the solution was concentrated to ca. 20 ml under reduced pressure. Partial neutralization with aq. Na2CO3 caused the product to separate as a gum, which soon solidified. The product was filtered, washed with water, and air-dried to give 1.1 g (80%) of 3-(γ, δ-dihydroxybutylamino)-4-phenoxy-5-sulfamylbenzoic acid as a colorless powder. A sample was recrystallized from methanol/water to give needles with mp 235°-238°; ir (Nujol) 3500, 3400, 2700 (broad) 1710, 1625, 1600, and 1525 cm-1 ; nmr (d 6 -DMSO) 1.5 (m, broad, 2H), 3.0-3.5 (m, broad, 5 H), 5.13 (s, broad, NH), 6.7-7.3 (m, C6H5), 7.17 (s, SO2NH2), 7.31 (d, J=2, CH), and 7.66 ppm, d, J=2, CH); mass spectrum m/e 378, 396 (M+).

Provenance & Evidence