Ammonia → HCID 12016015, compound

Temperature

60 °C

To a solution of (3aS, 4S, 6R, 6aR)-6-benzyloxy-2,2-dimethyltetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (588.6 mg, 2 mmol) in methanol (8.8 mL) was added methanesulfonic acid (0.007 mL, 0.1 mmol), and the mixture was stirred with heating to 60° C. for 24 hours. After the solution was dried under reduced pressure, ethyl acetate (2.9 mL) and 2,2-dimethoxypropane (0.17 mL, 1.4 mmoL) were added to the resulting oil, and the mixture was stirring at ambient temperature for 2 hours. Aqueous 7% sodium hydrogen carbonate solution (0.5 mL) was added for layer separation, and the resulting organic layer was concentrated under reduced pressure, to which was added aqueous 28% ammonia (1.2 mL, 20 mmol), and the mixture was stirred at ambient temperature for 14 hours. To the resulting solution was added ethyl acetate (3 mL) for layer separation, and the organic layer was concentrated under reduced pressure. To the resulting solid was added a hexane/ethyl acetate (3:1) solution (3 mL) for rinsing as a slurry at ambient temperature for 2 hours. Subsequently, the solid was filtered and rinsed in a hexane/ethyl acetate (3:1) solution (0.5 mL). The solid was dried under reduced pressure to recover (3aS, 4S, 6R, 6aR)-6-methoxy-2,2-dimethyltetrahydro-furo[3,4-d][1,3]dioxol-4-carboxylic acid amide (278.7 mg; yield of 64.2%) as a white solid. Melting point: 136° C.

1. dry with materialAfter the solution was dried under reduced pressure, ethyl acetate (2.9 mL) and 2,2-dimethoxypropane (0.17 mL, 1.4 mmoL)
2. additionwere added to the resulting oil
3. stirringthe mixture was stirring at ambient temperature for 2 hours
4. additionAqueous 7% sodium hydrogen carbonate solution (0.5 mL) was added for layer separation
5. concentrationthe resulting organic layer was concentrated under reduced pressure, to which
6. stirringthe mixture was stirred at ambient temperature for 14 hours
7. customfor layer separation
8. concentrationthe organic layer was concentrated under reduced pressure
9. additionTo the resulting solid was added a hexane/ethyl acetate (3:1) solution (3 mL)
10. washfor rinsing as a slurry at ambient temperature for 2 hours
11. filtrationSubsequently, the solid was filtered
12. washrinsed in a hexane/ethyl acetate (3:1) solution (0.5 mL)
13. customThe solid was dried under reduced pressure

ORD record

ord-e2e7680225a9403bb2dd5bd835dc8d6c

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06800742B2