Ethyl Acetate → HCID 86598331, compound

HRID 1393388Notes

Reaction equation

HRID 1393388 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)CCC.[CH2:20]([O:22][C:23](=[O:47])[C@H:24]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([O:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42](Br)[CH:41]=2)[CH:34]=1)[NH:25][C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[CH3:21].C(OCC)(=O)C>O1CCOCC1>[CH2:20]([O:22][C:23](=[O:47])[C@H:24]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([O:39][C:40]2[CH:41]=[CH:42][CH:43]=[C:44]([C:6]3[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=3)[CH:45]=2)[CH:34]=1)[NH:25][C:26](=[O:31])[C:27]([F:29])([F:30])[F:28])[CH3:21]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 27373184-(Tri-n-butylstannyl)pyridineHCID 86598332HCID 86598332, compound

Product 1

HCID 86598331HCID 86598331, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4-(tributylstannyl)pyridine (288 mg, 0.782 mmol) in degassed 1,4-dioxane (1 ml) and tetrakis(triphenyl-phosphine)palladium (46 mg, 0.04 mmol) were added in turn to a solution of 3-(3-bromophenoxy)-N-trifluoroacetyl-L-phenylalanine ethyl ester (360 mg, 0.782 mmol) in degassed 1,4-dioxane (6 ml) at room temperature and the mixture was stirred under heating for 8 hrs. After the mixture was cooled to room temperature, ethyl acetate was added thereto and the mixture was washed with saturated sodium fluoride solution, water and brine in turn and then dried. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1) to give N-trifluoroacetyl-3-[3-(4-pyridyl)phenoxy]-L-phenylalanine ethyl ester (235 mg, 66%) as colorless resinous substance.

Workup

  1. temperatureunder heating for 8 hrs
  2. washthe mixture was washed with saturated sodium fluoride solution, water and brine in turn
  3. customdried
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1)

Sources & evidence

ORD record
ord-2d68603bdb424d8ab7a2c93c50549bef
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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