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

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).

1. stirringAfter stirring for additional 2 h at r.t.
2. extractionextracted with AcOEt
3. dry with materialThe combined extracts are dried over MgSO4
4. concentrationconcentrated under reduced pressure
5. customThe residue is purified by column chromatography on silica gel (eluent; AcOEt:n-hexane=1:1)

ORD record

ord-2b87390f90104f7da09e3e35edbc5398

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07138432B1