HCID 10644854, compound → (S)-3-Amino-4-phenylbutanoic acid

HRID 1066017Notes

Reaction equation

HRID 1066017 reaction equation
C([O:8][C:9](=[O:30])[CH2:10][C@@H:11]([NH:19]C(OCC1C=CC=CC=1)=O)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C1C=CC=CC=1>CO>[NH2:19][C@@H:11]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][C:9]([OH:30])=[O:8]

Participants

3

Reactant 1

HCID 10644854HCID 10644854, compound

Product 1

HCID 2761537(S)-3-Amino-4-phenylbutanoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 3(S)-{{(benzyloxy)carbonyl}amino}-4-phenylbutyric acid benzyl ester (from step A) (10.97 g, 27.2 mmol) in MeOH (1 L) was stirred at room temperature for 7 h under an hydrogen atmosphere (1 atmosphere) in the presence of 20% Pd (OH)2/C (50 mg). The catalyst was removed by filtration through diatomaceous earth. The filtrate was concentrated under reduced pressure to yield 4.53 g (93% yield) of 3(S)-amino-4-phenylbutyric acid as a white solid. A suspension of NaHCO3 (12.74 g, 152 mmol) in MeCN (1.55 L) was stirred and heated to gentle reflux. Mesyl chloride (2.15 mL, 27.8 mmol) was added, followed by the portionwise addition of the preceding acid (4.53 g, 25.3 mmol) over 5 h. After 16 h under reflux, the solid was removed by filtration at 60° and the filtrate was concentrated under reduced pressure. The residual solid was triturated with EtOAc and filtered. The filtrate was concentrated and the residue purified by flash chromatography (SiO2, 40% EtOAc in hexane) to give 4(S)-benzylazetidin-2-one (2.20 g, 54% yield) as a white solid. 1H-NMR (400 MHz, CDCl3) δ7.35-7.17 (m, 5H), 5.83 (brs, 1H), 3.88-3.82 (m, 1H), 3.08 (ddd, J=14.8, 5.0, 2.2 Hz, 1H), 2.98 (dd, J=13.7, 5.7 Hz, 1H), 2.84 (dd, J=13.7, 7.9 Hz, 1H), 2.70 (ddd, J=14.9, 2.0, 1.3 Hz, 1H).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-75051b0a5c964b74aea55885e6b27bdd
Source dataset
uspto-grants-2001_06
Patent number
US06242439B1

Reaction notes

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