Pyridine → HCID 86598323, compound

HRID 1393378Notes

Reaction equation

HRID 1393378 reaction equation
N1C=CC=CC=1.[CH2:7]([O:9][C:10](=[O:27])[C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=1)[NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH3:8].[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1B(O)O>C(Cl)Cl.C(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:7]([O:9][C:10](=[O:27])[C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:30]2[CH:29]=[CH:28][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)[CH:21]=1)[NH:12][C:13](=[O:18])[C:14]([F:15])([F:16])[F:17])[CH3:8]

Participants

7

Reactant 3

HCID 1049PyridineHCID 2734375(Naphthalen-2-yl)boronic acidHCID 86598324HCID 86598324, compound

Product 1

HCID 86598323HCID 86598323, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridine (0.22 ml, 2.72 mmol) was added to a suspension of N-trifluoroacetyl-3-hydroxy-L-phenylalanine ethyl ester (159 mg, 0.521 mmol), 2-naphthaleneboronic acid (186 mg, 1.08 mmol), molecular sieves 4A powder (204 mg) and copper (II) acetate (153 mg, 0.842 mmol) in methylene chloride (7 ml) and the mixture was stirred under air atmosphere (without argon) at room temperature for 16 hrs. The reaction mixture was diluted with ethyl acetate (30 ml) and the insoluble materials were filtered off (celite (Trade mark)) and washed with ethyl acetate. The filtrate and washings were combined and washed with 10% hydrochloric acid and brine in turn and then dried. The solvent was distilled off under reduced pressure. The resultant residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=10) to give N-trifluoroacetyl-3-(2-naphthyloxy)-L-phenylalanine ethyl ester (200 mg, 89%) as pale yellow crystals.

Workup

  1. filtrationthe insoluble materials were filtered off (celite (Trade mark))
  2. washwashed with ethyl acetate
  3. washwashed with 10% hydrochloric acid and brine in turn
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe resultant residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=10)

Sources & evidence

ORD record
ord-2fcec40b2ae74e92a2fab8d675e23347
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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