Pyridine → HCID 86618207, compound

HRID 1669503Notes

Reaction equation

HRID 1669503 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[C:22]1([O:28][C:29]2[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:9]([O:8][C:6]([NH:5][C@@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:32]2[CH:33]=[CH:34][C:29]([O:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:30][CH:31]=2)=[CH:16][CH:15]=1)[C:3]([O:2][CH3:1])=[O:21])=[O:7])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 3

HCID 1049PyridineHCID 27343774-Phenoxyphenylboronic acidHCID 7019130Boc-Tyr-OMe

Product 1

HCID 86618207HCID 86618207, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-L-Tyrosine methyl ester (2.37 g, 8.0 mmol), 4-phenyoxyphenylboronic acid (2.57 g, 12.0 mmol) and pyridine (3.16 g) in CH2Cl2 (200 mL) was added copper(II) acetate (1.46 g, 8.0 mmol). After stirring at rt for 24 h, the reaction mixture was concentrated in vacuo. The remaining material was dissolved in EtOAc (200 mL) and this solution was washed with water (2×100 mL). The organic layer was concentrated in vacuo and the crude product was purified by chromatography (7:3 hexane/ethyl acetate) to give 2.39 g of product (64%). 1H NMR (400 MHz, CDCl3) δ 1.42 (s, 9H), 2.95-3.14 (m, 2H), 3.72 (s, 3H), 4.57 (q, J=7.2 Hz, 1H), 5.00 (br d, J=8.0 Hz, 1H), 6.90-7.11 (m, 11H), 7.30-7.36 (m, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe remaining material was dissolved in EtOAc (200 mL)
  3. washthis solution was washed with water (2×100 mL)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe crude product was purified by chromatography (7:3 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-046d472700944cdfb79a88391107aff5
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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