Potassium Phosphate, Tribasic → HCID 86598334, compound

HRID 1393390Notes

Reaction equation

HRID 1393390 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:22]([O:24][C:25](=[O:49])[C@H:26]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37](OS(C(F)(F)F)(=O)=O)[CH:36]=1)[NH:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])[CH3:23]>C(COC)OC.C(OCC)(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:22]([O:24][C:25](=[O:49])[C@H:26]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH:36]=1)[NH:27][C:28](=[O:33])[C:29]([F:30])([F:31])[F:32])[CH3:23]

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734375(Naphthalen-2-yl)boronic acidHCID 86598333HCID 86598333, compound

Product 1

HCID 86598334HCID 86598334, compoundYield 61%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

2-Naphthaleneboronic acid (142 mg, 0.824 mmol), tetrakis(triphenylphosphine)palladium (80 mg, 0.069 mmol) and potassium phosphate (120 mg, 0.563 mmol) were added in turn to a solution of N-trifluoroacetyl-3-trifluoromethane-sulfonyloxy-L-phenylalanine ethyl ester (300 mg, 0.686 mmol) in degassed dimetoxyethane (2 ml). The mixture was stirred under argon atmosphere at 85° C. for 3 hrs. After being cooled to room temperature, the reaction mixture was diluted with ethyl acetate and water and then extracted with ethyl acetate. The extract was washed with water and brine in turn and dried. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=9) to give N-trifluoroacetyl-3-(2-naphthyl)-L-phenylalanine ethyl ester (173 mg, 61%) as colorless crystals.

Workup

  1. temperatureAfter being cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine in turn
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=9)

Sources & evidence

ORD record
ord-409cfacbded341268b2f9b905e8cc0fc
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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