1-Hydroxybenzotriazole → N-(1-ethoxy-1-methyl ethoxy) acetamide

Participants

Reaction Steps

To a solution of 0.425 g (1 mmol) of desired {[4-(4-fluorobutoxy)-benzenesulfonyl](4-methoxy-benzyl)-amino}-acetic acid and 0.27 g (2 mmol) of HOBT in 4 ml of DMF, a solution of 0.116 g of O-(1-methoxy-1-methyl-ethyl)-hydroxylamine in 1 ml of DMF and 0.23 g of WSCD were successively added at 0–5° C. and the mixture was stirred for 1 h. After stirring for additional 2 h at r.t., the mixture is diluted with H2O and extracted with AcOEt. The combined extracts are dried over MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; AcOEt:n-hexane=1:1) to give 2-{[4-(4-fluorobutoxy)-benzenesulfonyl]-4-methoxy-benzyl)-amino}-N-(1-ethoxy-1-methyl ethoxy) acetamide; NMR (CDCl3): 1.35 (s, 6H), 1.83–2.0 (m, 4H), 3.29 (s, 3H), 3.70 (s, 2H), 3.78 (s, 3H), 4.08–4.11 (m, 2H), 4.32 (s, 2H), 4.47–4.49 (m, 1H), 4.60 (br s, 1H), 6.80–6.90 (m, 2H), 6.95–7.05 (m, 2H), 7.10–7.25 (m, 2H), 7.79 (d, 2H, J=9.06 Hz), 8.46 (br s, 1H).

Provenance & Evidence