Citric Acid → HCID 84014952, compound

HRID 2284732Notes

Reaction equation

HRID 2284732 reaction equation
C(=[N:8]/[C:9]([CH3:21])([CH3:20])[CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])\C1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1>[NH2:8][C:9]([CH3:21])([CH3:20])[CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 178483526HCID 178483526, compound

Product 1

HCID 84014952HCID 84014952, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-tert-butyl (2-(benzylideneamino)-2-methylpropyl)(methyl)carbamate (G9, 3.17 g) in tetrahydrofuran (25 mL), 5% aqueous citric acid (25 mL) was added at room temperature, and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added. The organic layer was separated, and the aqueous layer was extracted with methylene chloride. The organic layer and the extract were combined, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate) to obtain tert-butyl (2-amino-2-methylpropyl)(methyl)carbamate (G10, 506 mg).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with methylene chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-1185940bf6454872a3b62ca2f78c8f6e
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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