HCID 58288271, compound → HCID 58288162, compound

HRID 1476105Notes

Reaction equation

HRID 1476105 reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]([CH2:16][CH:17]([CH:25]2[CH2:27][CH2:26]2)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:12]=[CH:13][C:14]=1[Cl:15])C1C=CC=CC=1>C(OCC)(=O)C>[NH2:8][C:9]1[CH:10]=[C:11]([CH2:16][CH:17]([CH:25]2[CH2:26][CH2:27]2)[C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

3

Reactant 1

HCID 58288271HCID 58288271, compound

Product 1

HCID 58288162HCID 58288162, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2.50 g (4.63 mmol) of (+/−)-tert-butyl 3-[3-(benzylamino)-4-chlorophenyl]-2-cyclopropylpropanoate were dissolved in 160 ml of ethyl acetate, the mixture was deoxygenated with argon and 150 mg of palladium on carbon (10%) were added. The reaction mixture was stirred at RT under an atmosphere of hydrogen at atmospheric pressure for 8 h. The mixture was then filtered through celite, the residue was washed with ethyl acetate, the filtrate was concentrated under reduced pressure and the residue was dried under high vacuum. The residue was purified by chromatography on silica gel (mobile phase pure cyclohexane to cyclohexane/ethyl acetate 20:1). This gave 1.41 g of the target product (73.6% of theory).

Workup

  1. customthe mixture was deoxygenated with argon and 150 mg of palladium on carbon (10%)
  2. additionwere added
  3. filtrationThe mixture was then filtered through celite
  4. washthe residue was washed with ethyl acetate
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was dried under high vacuum
  7. customThe residue was purified by chromatography on silica gel (mobile phase pure cyclohexane to cyclohexane/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-1ccf33c5e7714905b6150a471fb9c0c6
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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