Ethyl Acetate → tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionate

To a mixture of tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-amino-propionate (1.02 g, 2.0 mmol), with trimethylsilyl cyanide (0.7 ml, 5.2 mmol) in dry acetonitrile (15 ml) was added methanesulfonyl chloride (0.18 ml, 2.3 mmol) and the material was stirred overnight. Ethyl acetate (80 ml) was added and the material was partitioned with aqueous hydrochloric acid (1.5%, 80 ml). The organic phase was collected and washed with an equal volume of brine; The aqueous phases were back extracted with ethyl acetate (2×80 ml) and the organic phases combined, dried (MgSO4), filtered and condensed to provide tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionate as a pale yellow semi-viscous oil (1.4 g).

1. customthe material was partitioned with aqueous hydrochloric acid (1.5%, 80 ml)
2. customThe organic phase was collected
3. washwashed with an equal volume of brine
4. extractionThe aqueous phases were back extracted with ethyl acetate (2×80 ml)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customcondensed

ORD-Eintrag

ord-e170b1045e454c7d8d342e66d2f0ad48

Quelldatensatz

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06787559B2