Water → N-Hydroxy-2-(6-methoxy-1,3,4,9-tetrahydro-beta-carboline-2-sulfonylmethyl)-3-methylbutyramide

1-(3-Dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (104 mg) was added to a slurry of 2-(6-methoxy-1,3,4,9-tetrahydro-β-carboline-2-sulfonylmethyl)-3-methylbutyric acid (172 mg) in dichloromethane (10 ml). The mixture was stirred for 5 minutes before addition of O-(t-butyldimethylsilyl)hydroxylamine (80 mg), then for 1.5 h. The mixture was poured into water (10 ml) and extracted with dichloromethane (3×15 ml). The combined organics were washed with water (2×50 ml), dried (MgSO4) and evaporated under reduced pressure. The residue was dissolved in dichloromethane (10 ml) and 1.0N hydrogen chloride in ether (2.5 ml) was added. The mixture was stirred at room temperature for 2 h. It was evaporated under reduced pressure and the residue chromatographed (SiO2, 5% methanol in dichloromethane) to give the title compound (37 mg, 21%) as a pale orange solid.

1. extractionextracted with dichloromethane (3×15 ml)
2. washThe combined organics were washed with water (2×50 ml)
3. dry with materialdried (MgSO4)
4. customevaporated under reduced pressure
5. dissolutionThe residue was dissolved in dichloromethane (10 ml)
6. addition1.0N hydrogen chloride in ether (2.5 ml) was added
7. customIt was evaporated under reduced pressure
8. customthe residue chromatographed (SiO2, 5% methanol in dichloromethane)

ORD record

ord-0287a690b71447aca00e2f440ce7ba8d

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06734189B2