HCID 131727291, compound → HCID 131727290, compound

HRID 1641499Notes

Reaction equation

HRID 1641499 reaction equation
C([NH:8][C:9]([NH:11][C:12]1([CH2:33][O:34][SiH3:35])[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:13]1[F:32])=[O:10])C1C=CC=CC=1>CC(O)=O.[Pd]>[C:28]([CH:14]1[C:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([CH2:33][O:34][SiH3:35])([NH:11][C:9](=[O:10])[NH2:8])[CH:13]1[F:32])([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 1

HCID 131727291HCID 131727291, compound

Product 1

HCID 131727290HCID 131727290, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×

Procedure

In the Parr Hydrogenator flask with 1 mL AcOH and 10% Pd/C 0.15 g inside, 1-benzyl-3-(3-tert-butyl-diphenyl-siloxymethyl-2-fluoro-cyclobutyl)-urea in 5 mL AcOH was added. This was hydrogenolysed at 50 psi for 4 d, after which the crude mixture was filtered through celite and was purified by silica gel flash chromatography (CH2Cl2: MeOH=40:1) to give 0.15 g (63.3%, Rf=0.44 (CH2Cl2: MeOH=20:1) the desired product. IR (neat) νmax 3425, 3339, 2931, 2858, 1656, 1608, 1560, 1111, 701.

Workup

  1. filtrationafter which the crude mixture was filtered through celite
  2. customwas purified by silica gel flash chromatography (CH2Cl2: MeOH=40:1)

Sources & evidence

ORD record
ord-ed3f9544d8144b369d3c6a67aee91700
Source dataset
uspto-grants-2012_02
Patent number
US08114994B2

Reaction notes

Loading…