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t-Butyloxycarbonylaspartic acid alpha-benzyl ester → 3-((tert-Butoxycarbonyl)amino)-4-methoxy-4-oxobutanoic acid

HRID 2236023
Notes
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Reaction equation

HRID 2236023 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 82036t-Butyloxycarbonylaspartic acid alpha-benzyl esterHCID 86587183Trimethylsilyldiazomethane hexane2×

Product 1

HCID 142587023-((tert-Butoxycarbonyl)amino)-4-methoxy-4-oxobutanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

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

  1. stirringwere stirred for 1 hour
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in 20 ml of ethanol
  4. addition2.0 g of palladium carbon (10% w/v) was added to the obtained solution, and they
  5. stirringwere stirred in hydrogen gas atmosphere for 19 hours
  6. filtrationAfter the filtration
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-820fcd280f6b478fbca844470f90d760
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07713957B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes