Potassium Carbonate → HCID 86598327, compound

HRID 1393381Notes

Reaction equation

HRID 1393381 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([O:21][C:22](=[O:39])[C@H:23]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([OH:38])[CH:33]=1)[NH:24][C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH3:20]>C(C(C)=O)C.[I-].[K+]>[CH2:19]([O:21][C:22](=[O:39])[C@H:23]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH2:2][C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=2)[CH:33]=1)[NH:24][C:25](=[O:30])[C:26]([F:27])([F:28])[F:29])[CH3:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 703202-BromomethylnaphthaleneHCID 86598324HCID 86598324, compound

Product 1

HCID 86598327HCID 86598327, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

2-(Bromomethyl)naphthalene (453 mg, 1.97 mmol), potassium carbonate (340 mg, 2.46 mmol) and potassium iodide (14 mg, 0.084 mmol) were added in turn to a solution of N-trifluoroacetyl-3-hydroxy-L-phenylalanine ethyl ester (500 mg, 1.64 mmol) in methyl ethyl ketone (20 ml) and the mixture was stirred under argon atmosphere at 60° C. for 14 hrs. The reaction mixture was cooled to room temperature and the insoluble materials were filtered off and washed with ethyl acetate. The filtrate and washings were combined and washed with water and brine 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=12) to give N-trifluoroacetyl-3-[(2-naphthyl)methoxy]-L-phenylalanine ethyl ester (576 mg, 79%) as colorless crystals.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe insoluble materials were filtered off
  3. washwashed with ethyl acetate
  4. washwashed with water and brine
  5. customdried
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified, by column chromatography on silica gel (n-hexane/ethyl acetate=12)

Sources & evidence

ORD record
ord-ddbf7459dc834492a22795166958cd63
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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