HCID 86612635, compound → HCID 86612634, compound

HRID 1881772Notes

Reaction equation

HRID 1881772 reaction equation
C([O:8][C:9]1[C:10](=[O:26])[N:11]([CH2:15][C:16](=[O:25])[NH:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>CCO.[Pd].[Fe+3]>[OH:8][C:9]1[C:10](=[O:26])[N:11]([CH2:15][C:16](=[O:25])[NH:17][O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 86612635HCID 86612635, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86612634HCID 86612634, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 29936Ferric cationCatalystHCID 702EthanolSolvent

Procedure

17 (350 mg, 0.8 mmol) was suspended in 175 mL of EtOH. 10% (w/w, 38 mg) of 10% Pd/C catalyst was added to the hydrogenation flask (500 mL Pyrex® Parr reaction bottle tested to 120 psi, max. working pressure of 60 psi). The Parr hydrogenation system located in the VanNieuwenhze lab was used for the deprotection reactions. The hydrogen pressure was set to 35 psi with agitation, and the process went on for 41 h. A white precipitate was present even after the reaction was stopped, but this white product reacted with iron(III) to give a reddish product instead of no reaction as seen with the protected starting material. The catalyst was removed by vacuum filtration and separated from the product by dissolving the white precipitate in 125 mL hot CH2Cl2 and MeOH and THF. The clear solution was concentrated by rotary evaporation to yield a white solid. The solid was washed with MeOH to remove residual DCU to yield a white, feathery microcrystalline solid. Yield: 57%. 1H NMR (d6-DMSO, 400 MHz, 25° C.): δ 4.75 (s, 2H, —CH2—), 6.11 (t, J=7.0 Hz, 1H, Ar—H), 6.72 (d, J=7.2 Hz, 1H, Ar—H), 6.97 (m, 4H, Phenoxy-H), 7.11 (m, 2H, Ar—H, Phenoxy-H), 7.36 (t, J=7.2 Hz, 2H, Phenoxy-H), 7.58 (d, J=6.8 Hz, 2H, Phenoxy-H), 9.03 (s, 1H, —OH), 10.36 (s, 1H, APCI-MS: m/z 336.9 [M+H]+. Anal. Calcd for C19H16N2O4: C, 67.85; H, 4.79; N, 8.33. Found: C, 67.75; H, 5.07; N, 8.49.

Workup

  1. customwent on for 41 h
  2. customto give a reddish product
  3. custominstead of no reaction
  4. customThe catalyst was removed by vacuum filtration
  5. customseparated from the product
  6. dissolutionby dissolving the white precipitate in 125 mL hot CH2Cl2
  7. concentrationThe clear solution was concentrated by rotary evaporation
  8. customto yield a white solid
  9. washThe solid was washed with MeOH
  10. customto remove residual DCU
  11. customto yield a white, feathery microcrystalline solid

Sources & evidence

ORD record
ord-1c266f646b05443e9b56aaeb9cebf067
Source dataset
uspto-grants-2012_11
Patent number
US08318945B2

Reaction notes

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