Dimethylformamide → N-hydroxy-2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3-methylbutyramide

To a solution of 2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)amino]-3-methylbutyric acid (3.82 g, 8.24 mmol) in dry methylene chloride (20 mL) was added oxalyl chloride (2.2 mL, 24.72 mmol) and a drop of dimethylformamide. The reaction mixture was stirred for 4 h and then concentrated. The residue was dissolved in methylene chloride (20 mL) and N,O-bis-trimethylsilylhydroxylamine (8.8 mL, 41.2 mmol) was added. After 4 h, methanol (1 mL) was added and the stirring was continued for 30 min. Silica gel (10 g) was added and the material was concentrated to dryness. The resultant powder was flash chromatographed on a silica gel column and eluted with 50% ethyl acetate/hexanes to give N-hydroxy-2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3-methylbutyramide (2.46 g).

1. concentrationconcentrated
2. dissolutionThe residue was dissolved in methylene chloride (20 mL)
3. waitAfter 4 h
4. waitthe stirring was continued for 30 min
5. additionSilica gel (10 g) was added
6. concentrationthe material was concentrated to dryness
7. customchromatographed on a silica gel column
8. washeluted with 50% ethyl acetate/hexanes

ORD-Eintrag

ord-298739ec5cfb43e193b7cf391821e1ab

Quelldatensatz

uspto-grants-2005_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06844366B2