1,1-Dimethylethyl (betaS)-beta-aminobenzenepropanoate → Methyl (S)-3-amino-3-phenylpropanoate

HRID 1823833Notes

Reaction equation

HRID 1823833 reaction equation
[NH2:1][C@H:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][C:4]([O:6][C:7](C)(C)C)=[O:5]>Cl>[CH3:7][O:6][C:4](=[O:5])[CH2:3][C@H:2]([NH2:1])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 70210931,1-Dimethylethyl (betaS)-beta-aminobenzenepropanoate

Product 1

HCID 788099Methyl (S)-3-amino-3-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

t-Butyl (3S)-3-amino-3-phenylpropanoate (1.0 g, 4.97 mmol) was dissolved in methanolic hydrochloric acid (2.25M, 25 ml). The reaction mixture was heated under reflux for 3 hours, after which time the solvent was evaporated under reduced pressure and the residue basified with aqueous saturated sodium carbonate solution. The product was then extracted using dichloromethane (x2), the combined organic layers were dried (MgSO4), filtered and the solvent removed under reduced pressure to afford the title compound as a white solid, 778 mg.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customafter which time the solvent was evaporated under reduced pressure
  4. extractionThe product was then extracted
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7b7c978dde6f45a9a766c891608f96e8
Source dataset
uspto-grants-2006_05
Patent number
US07041667B1

Reaction notes

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