Allyl bromide → Allyl 2-(acetylamino)-3-(4-amino-3-ethylphenyl)propanoate

HRID 488638Notes

Reaction equation

HRID 488638 reaction equation
[C:1]([NH:4][C@H:5]([C:16]([OH:18])=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([CH2:14][CH3:15])[CH:8]=1)(=[O:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:25](Br)[CH:26]=[CH2:27]>CN(C)C=O>[C:1]([NH:4][CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([CH2:14][CH3:15])[CH:8]=1)[C:16]([O:18][CH2:27][CH:26]=[CH2:25])=[O:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 69800149N-acetyl-4-amino-3-ethylphenylalanine

Product 1

HCID 11130033Allyl 2-(acetylamino)-3-(4-amino-3-ethylphenyl)propanoateYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-acetyl-4-amino-3-ethylphenylalanine (2.0 g, 8.0 mmol), Cs2CO3 (2.61 g, 8.0 mmol) and allyl bromide (692 μL, 8.0 mmol) in N,N-dimethylformamide (40 mL) was stirred at room temperature for 3 hours, concentrated under reduce pressure and partitioned between ethyl acetate and water (100 mL, 1:1). The organic phase was washed with brine (1×50 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by on silica gel with ethyl acetate/hexane (5:3) to provide titled compound (1.44 g). MS (ESI(+)) m/e 291 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.23 (d, 1H), 6.77-6.70 (m, 2H), 6.50 (d, 1H), 5.90-5.76 (m, 1H), 5.30-5.15 (m, 2H), 4.67 (s, 2H), 4.54-4.50 (m, 2H), 4.38-4.30 (m, 1H), 2.77(dddd, 2H), 2.39 (q, 2H), 1.80 (s, 3H), 1.10 (t, 3H).

Workup

  1. concentrationconcentrated
  2. custompartitioned between ethyl acetate and water (100 mL, 1:1)
  3. washThe organic phase was washed with brine (1×50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by on silica gel with ethyl acetate/hexane (5:3)

Sources & evidence

ORD record
ord-b8e65754e05d42849699fd2b7f7c2f0a
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

Loading…