Pyridine → HCID 86601875, compound

HRID 600189Notes

Reaction equation

HRID 600189 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:26][C@@H:27]1[C@@H:68]([O:69][C:70](=[O:72])[CH3:71])[C@H:67]([O:73][C:74](=[O:76])[CH3:75])[C@@H:66]([C:77]([O:79][CH3:80])=[O:78])[O:65][C@H:28]1[O:29][C:30]1[CH:35]=[CH:34][C:33]([C@@H:36]2[C@@H:39]([CH2:40][CH2:41][C@H:42]([O:50][C:51](=[O:53])[CH3:52])[C:43]3[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=3)[C:38](=[O:54])[N:37]2[C:55]2[CH:60]=[CH:59][C:58]([C:61]#[C:62][CH2:63][OH:64])=[CH:57][CH:56]=2)=[CH:32][CH:31]=1)(=[O:25])[CH3:24].N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[C:23]([O:26][C@@H:27]1[C@@H:68]([O:69][C:70](=[O:72])[CH3:71])[C@H:67]([O:73][C:74](=[O:76])[CH3:75])[C@@H:66]([C:77]([O:79][CH3:80])=[O:78])[O:65][C@H:28]1[O:29][C:30]1[CH:35]=[CH:34][C:33]([C@@H:36]2[C@@H:39]([CH2:40][CH2:41][C@H:42]([O:50][C:51](=[O:53])[CH3:52])[C:43]3[CH:44]=[CH:45][C:46]([F:49])=[CH:47][CH:48]=3)[C:38](=[O:54])[N:37]2[C:55]2[CH:60]=[CH:59][C:58]([C:61]#[C:62][CH:63]=[O:64])=[CH:57][CH:56]=2)=[CH:32][CH:31]=1)(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 1049PyridineHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86601876HCID 86601876, compound

Product 1

HCID 86601875HCID 86601875, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (33.0 mg, 0.077 mmol) was added to a solution of 10b (62.0 mg, 0.077 mmol) and pyridine (31.0 μL, 0.386 mmol) in dichloromethane (1 mL) at room temperature. After 30 min, the reaction mixture was poured into saturated aqueous sodium bicarbonate, and extracted twice with ethyl acetate. The combined organic extracts were washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 20-40% ethyl acetate/hexanes) afforded the title compound 10c.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 20-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9be308770fd343a59b012eddb4f703d8
Source dataset
uspto-grants-2011_03
Patent number
US07901893B2

Reaction notes

Loading…