Hydrochloric Acid → HCID 51615675, compound

HRID 899442Notes

Reaction equation

HRID 899442 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C@:4]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[N:5]=C(C1C=CC=CC=1)C1C=CC=CC=1.Cl>CO>[CH3:1][O:2][C:3](=[O:30])[C@:4]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH2:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 87354237Methyl-alpha-butyl-n-(diphenylmethylene)phenylalaninate

Product 1

HCID 51615675HCID 51615675, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl-α-butyl-N-(diphenylmethylene)phenylalaninate (0.31 g, 0.78 mmol) from step A in 10 mL MeOH was added 3.33M hydrochloric acid (0.69 mL, 2.3 mmol). After 1.5 h at rt, the reaction was concentrated in vacuo to remove volatiles, then redissolved in saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc (2×), the combined organics were washed with water, brine, dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (20 g silica, 0->30% EtOAc/hexanes) afforded methyl-α-butylphenylalaninate as a viscous oil. 1H NMR (400 MHz, d4-MeOH) δ 7.30-7.23 (m, 3H), 7.14-7.12 (m, 2H), 3.68 (d, J=13.1, 1H), 3.18 (d, J=13.1, 1H), 1.92 (m, 1H), 1.61 (m, 1H), 1.51-1.32 (m, 3H), 1.12 (m, 1H) M+H=236.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customto remove volatiles
  3. dissolutionredissolved in saturated aqueous NaHCO3
  4. extractionThe aqueous layer was extracted with EtOAc (2×)
  5. washthe combined organics were washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (20 g silica, 0->30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9a482b58eb174fbabe1ded34631fbf94
Source dataset
uspto-grants-2008_04
Patent number
US07354942B2

Reaction notes

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