Triethylamine → HCID 69159146, compound

HRID 1057512Notes

Reaction equation

HRID 1057512 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11][CH2:12]/[CH:13]=[CH:14]/[C:15]([O:17][CH3:18])=[O:16])[C:5](Br)=[CH:6][CH:7]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]2[C:13](=[CH:14][C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][N:10]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:9][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 131723754HCID 131723754, compound

Product 1

HCID 69159146HCID 69159146, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring solution of methyl (2E)-5-{N-[(3-amino-6-bromophenyl)methyl](tert-butoxy)carbonylamino}pent-2-enoate (1 eq) in toluene (0.08 M) at room temperature was added tetrakis(triphenylphosphine) palladium(0.03 eq) and triethylamine (3 eq). The reaction mixture was stirred at 100° C. for 18 hr and filtered through celite. The reaction solvent was removed by rotary evaporation. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic phase was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (30% EtOAc/Hexane). EI-MS m/z 333 (M+H)+.

Workup

  1. filtrationfiltered through celite
  2. customThe reaction solvent was removed by rotary evaporation
  3. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (30% EtOAc/Hexane)

Sources & evidence

ORD record
ord-ebb3af524d694fdeb3fbeb4d28ba2a43
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

Loading…