Neopentylamine → HCID 178449110, compound

Participants

Reaction Steps

To a solution of {1-benzyl-3-[(3-dimethylaminomethylene-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 21 (32mg, 0.05 mmol) in absolute ethanol (1 ml) was added neopentylamine (29 μl, 0.25 mmol). The resulting solution was stirred 22 h and then concentrated in vacuo. The residue was purified on a preparative TLC plate (20×20 cm, 500 μm) using 8:2 ethyl acetate:hexane as eluant to provide [1-benzyl-3-({3-[(2,2-dimethyl-propylamino)-methylene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl}-isobutyl-amino)-2-hydroxy-propyl]-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 22 (24 mg, 70%). TLC: Rf 0.63 (ethyl acetate:hexanes). MS m/z 685 (MH)+. 1H NMR (CDCl3) is consistent with structure.

Provenance & Evidence