t-Butyloxycarbonylaspartic acid alpha-benzyl ester → 3-((tert-Butoxycarbonyl)amino)-4-methoxy-4-oxobutanoic acid
Reaction equation
C([O:8][C:9](=[O:23])[CH2:10][CH:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:12]([OH:14])=[O:13])C1C=CC=CC=1.[CH3:24][Si](C=[N+]=[N-])(C)C.CCCCCC>CO.C1(C)C=CC=CC=1>[C:19]([O:18][C:16]([NH:15][CH:11]([C:12]([O:14][CH3:24])=[O:13])[CH2:10][C:9]([OH:8])=[O:23])=[O:17])([CH3:22])([CH3:21])[CH3:20]Participants
Procedure
2.0 g (6.18 mmol) of 4-(benzyloxy)-2-[(t-butoxycarbonyl)amino]-4-oxobutanoic acid was dissolved in a solvent mixture of 6 ml of methanol and 12 ml of toluene. 3.7 ml of 2 M trimethylsilyldiazomethane/hexane solution was added to the obtained solution and they were stirred for 3 hours. Additional 0.5 ml of 2 M trimethylsilyldiazomethane/hexane solution was added to the reaction mixture and they were stirred for 1 hour. The solvent was evaporated under reduced pressure. The residue was dissolved in 20 ml of ethanol. 2.0 g of palladium carbon (10% w/v) was added to the obtained solution, and they were stirred in hydrogen gas atmosphere for 19 hours. After the filtration, the solvent was evaporated under reduced pressure to obtain the title compound.
Workup
- stirringwere stirred for 1 hour
- customThe solvent was evaporated under reduced pressure
- dissolutionThe residue was dissolved in 20 ml of ethanol
- addition2.0 g of palladium carbon (10% w/v) was added to the obtained solution, and they
- stirringwere stirred in hydrogen gas atmosphere for 19 hours
- filtrationAfter the filtration
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-00b88a3bd2a74913898266f74d622d8e
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278329B2
Reaction notes
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