HCID 67609216, compound → HCID 67506182, compound

HRID 1965188Notes

Reaction equation

HRID 1965188 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:10]2[N:22](C(OCC3C=CC=CC=3)=O)[CH2:23][CH2:24][CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[CH:10]2[NH:22][CH2:23][CH2:24][CH:9]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 67609216HCID 67609216, compound

Product 1

HCID 67506182HCID 67506182, compoundYield 123.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 44 (3.40 g, 7.22 mmol) in MeOH (70 mL) was added NH4OAc (280 mg, 3.61 mmol) and 10% Pd-on-carbon (wet, 770 mg, 0.70 mmol). The reaction flask was evacuated and backfilled with hydrogen (4×) and then maintained under a balloon of hydrogen gas. After 90 min, the catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in Et2O and washed successively with saturated aqueous NaHCO3, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 3.0 g of 45 as a colorless oil which was used in the next step without further purification. Mass spectrum, m/z [336.7] (M+H)+.

Workup

  1. customThe reaction flask was evacuated
  2. temperaturemaintained under a balloon of hydrogen gas
  3. customthe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in Et2O
  6. washwashed successively with saturated aqueous NaHCO3, and brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d4c5ffd2d92e4ad9b15b0275631d96bb
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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