Triethylamine → HCID 67352364, compound

HRID 1669497Notes

Reaction equation

HRID 1669497 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].[O:22]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:32]2[CH:33]=[CH:34][C:29]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:30][CH:31]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343774-Phenoxyphenylboronic acidHCID 7016055Boc-D-Tyr-OMe

Product 1

HCID 67352364HCID 67352364, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-D-Tyrosine-Methyl ester (0.150 g, 0.508 mmol), 4-Phenoxyphenyl-boronic acid (0.109 g, 0.508 mmol), and triethylamine (0.355 mL, 2.539 mmol) in anhydrous dichloromethane (DCM) (12.5 mL) at room temperature under an atmosphere of nitrogen was added copper (II) acetate (0.070 g, 0.508 mmol), and the resulting mixture was stirred at room temperature for about 18 h. The reaction mixture was washed with 20 mL of water and 20 mL of DCM and filtered. The DCM layer was then extracted. The aqueous layer was re-extracted with DCM (2×15 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and the solvent was removed in vacuo to obtain the crude mixture, which was purified by of silica gel flash chromatography, using ethyl acetate (EtOAc)/hexane (gradient system), to obtain the product (110 mg, 47%): 1H NMR (400 MHz, CDCL3): δ 1.42 (s, 9H), 2.98-3.09 (m, 2H), 3.71 (d, J=5.2 Hz), 4.55-4.58 (m, 1H), 4.98-5.01 (m, 1H), 6.75 (d, 1H, J=8.4 Hz), 6.91-7.02 (m, 6H), 7.07-7.11 (m, 3H), 7.31-7.35 (m, 2H); MS: m/z 364 (MH)+ & no -boc group, m/z 464 (MH)+.

Workup

  1. washThe reaction mixture was washed with 20 mL of water and 20 mL of DCM
  2. filtrationfiltered
  3. extractionThe DCM layer was then extracted
  4. extractionThe aqueous layer was re-extracted with DCM (2×15 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customto obtain the crude mixture, which
  9. customwas purified by of silica gel flash chromatography

Sources & evidence

ORD record
ord-a2964b173ed348e4b0c8a5d3a3fa8f93
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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