Acetic Anhydride → HCID 69076131, compound

HRID 458764Notes

Reaction equation

HRID 458764 reaction equation
[F:1][C:2]1([F:33])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:32])([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][OH:31])=[CH:26][CH:25]=2)[C:8]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[O:9])[CH2:3]1.CN(C1C=CC=CN=1)C.[C:43](OC(=O)C)(=[O:45])[CH3:44]>C(Cl)(Cl)Cl.C(N(CC)CC)C.C(OCC)(=O)C>[F:33][C:2]1([F:1])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:32])([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][O:31][C:43](=[O:45])[CH3:44])=[CH:26][CH:25]=2)[C:8]([O:10][CH:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]2)=[O:9])[CH2:3]1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 69075646HCID 69075646, compound

Product 1

HCID 69076131HCID 69076131, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 42 mg of t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-(hydroxymethyl)phenyl)-ethanoyloxy)tetrahydropyridine-1(2H)-carboxylate in 2 ml of chloroform, 0.015 ml of triethylamine, 0.01 ml of acetic anhydride and 2 mg of dimethylaminopyridine were added successively, followed by an hour's stirring at room temperature. The reaction liquid was diluted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the resulting residue was purified on preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), hexane/ethyl acetate=2/1) to provide 42 mg of the title compound as a colorless oily substance.

Workup

  1. waitfollowed by an hour
  2. customThe reaction liquid
  3. washwashed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationDistilling the solvent off under reduced pressure
  6. customthe resulting residue was purified on preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-03056d3e2548489e89164c4890531529
Source dataset
uspto-grants-2007_03
Patent number
US07192969B2

Reaction notes

Loading…