HCID 24948000, compound → HCID 59485856, compound

HRID 1972200Notes

Reaction equation

HRID 1972200 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=4)[C@H:16]([CH2:26][O:27]CC4C=CC=CC=4)[O:15][C:14]3=[O:35])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[H][H]>C(O)C.C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=4)[C@H:16]([CH2:26][OH:27])[O:15][C:14]3=[O:35])=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24948000HCID 24948000, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59485856HCID 59485856, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

The title compound was obtained as a colorless oil from 1-((E)-3-(benzyloxy)prop-1-enyl)-3,5-difluorobenzene by the same method that is described for Example 39. (4S,5R)-3-(4-(4-chlorophenoxy)phenyl)-5-((benzyloxy)methyl)-4-(3,5-difluorophenyl)oxazolidin-2-one (Example 96) was placed into a 25 mL round bottom flask and dissolved in 7 mL ethanol:ethyl acetate (1:1) and treated with palladium on carbon (10% by weight, 73 mg). The vessel was sealed with a rubber septum and charged with hydrogen. The reaction was stirred for 2 h, then filtered on celite, evaporated to dryness and purified on silica gel (20-30% ethyl acetate/hexanes) to give the title compound as a colorless oil that solidified on standing. 1H NMR (acetone-d6) δ (ppm) 7.53 (d, J=9.1 Hz, 2H), 7.37 (d, J=9.0 Hz, 2H), 7.21-7.16 (m, 2H), d, J=6.15 Hz, 2H), 7.02-6.93 (m, 5H), 5.58 (d, J=5.4 Hz, 1H), 4.55 (t, J=5.8 Hz, 1H), 4.45 (ddd, J=5.6, 3.7, 3.6), 3.97 (ddd, J=12.3, 5.6, 3.8 Hz, 1H), 3.90 (ddd, J=12.3, 5.6, 3.8 Hz, 1H); HPLC-MS calculated C22H16ClF2NO4 (M+H+): 432.1, found: 432.0.

Workup

  1. customThe vessel was sealed with a rubber septum
  2. filtrationfiltered on celite
  3. customevaporated to dryness
  4. custompurified on silica gel (20-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4dd75f2218cf48b583d890e8dd1d769f
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

Loading…