Pyridine → HCID 54454033, compound

HRID 726864Notes

Reaction equation

HRID 726864 reaction equation
[CH3:1][N:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[CH:3]1[CH2:4][C@H:5]([CH3:23])[C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[OH:22].N1C=CC=CC=1.[C:30](Cl)(=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32]>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:30]([O:22][C@H:10]1[CH2:9][CH2:8][C@H:7]2[C@H:6]3[C@H:15]([CH2:14][CH2:13][C@:11]12[CH3:12])[C@:16]1([CH3:21])[CH:3]([N:2]([CH3:1])[C:19](=[O:20])[CH2:18][CH2:17]1)[CH2:4][C@@H:5]3[CH3:23])(=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32]

Participants

7

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chloride2×HCID 22861808HCID 22861808, compound

Product 1

HCID 54454033HCID 54454033, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 70 from Example 69, being 60.2 mg in 4 ml methylene chloride and 200 ml pyridine was added 15 mg DMAP (4-dimethylaminopyridine) followed by 68.66 mg pivaloyl chloride, i.e., trimethyl acetyl chloride. After stirring for 24 hours, the reaction mixture was diluted with ethyl acetate, washed with water, then aqueous sodium carbonate and brine. The organic layer was dried, concentrated to a residue, which was purified by preparative chromatography on silica gel using 3:1 chloroform/acetone as eluant to yield pure title compound 71 Proton NMR confirmed the assigned structure.

Workup

  1. washwashed with water
  2. customThe organic layer was dried
  3. concentrationconcentrated to a residue, which
  4. customwas purified by preparative chromatography on silica gel using 3:1 chloroform/acetone as eluant

Sources & evidence

ORD record
ord-164a26b0573449cd862b7c1673e6b344
Source dataset
uspto-grants-1998_01
Patent number
US05710275

Reaction notes

Loading…