Ammonia → HCID 68621615, compound

HRID 1620048Notes

Reaction equation

HRID 1620048 reaction equation
ClC(OCC(C)C)=O.[CH2:9]([O:16][C:17]([NH:19][C@@H:20]([C:25]([OH:27])=O)[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1([NH:34]C2CCCCC2)CCCCC1.CN1CCOCC1.N.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.COCCOC>[CH2:9]([O:16][C:17]([NH:19][C@@H:20]([C:25]([NH2:34])=[O:27])[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 44629899HCID 44629899, compound

Product 1

HCID 68621615HCID 68621615, compoundYield 111.4%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Isobutyl chloroformate (811 μl) was added dropwise to a mixture of N-benzyloxycarbonyl-D-leucine•dicyclohexylamine salt (2.23 g), 1,2-dimethoxyethane (25 ml), and N-methylmorpholine (687 μl) under ice cooling, followed by stirring at the same temperature for 1 hour. 25% aqueous ammonia solution (3.4 ml) was added to the reaction mixture under ice cooling, followed by stirring at the same temperature for 1 hour. A saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the reaction mixture. The organic layer was collected, washed with saturated saline, and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. Hexane was added to the obtained residue and solid matter was collected by filtration, and a white solid of N2-benzyloxycarbonyl-D-leucinamide (1.47 g) was thus obtained.

Workup

  1. stirringby stirring at the same temperature for 1 hour
  2. customThe organic layer was collected
  3. washwashed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. additionHexane was added to the obtained residue and solid matter
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-f806e97107f24f0b86a7006de45608f4
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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