Citric Acid → HCID 89635780, compound

HRID 1476772Notes

Reaction equation

HRID 1476772 reaction equation
O[Li].O.[Si]([O:11][C@H:12]1[CH2:16][N:15]([C:17]2[CH:22]=[CH:21][N:20]3[N:23]=[CH:24][C:25]([C:26]([O:28]CC)=[O:27])=[C:19]3[CH:18]=2)[C@@H:14]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[F:38])[CH2:13]1)(C(C)(C)C)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCO.O>[F:38][C:32]1[CH:33]=[CH:34][C:35]([F:37])=[CH:36][C:31]=1[C@H:14]1[CH2:13][C@@H:12]([OH:11])[CH2:16][N:15]1[C:17]1[CH:22]=[CH:21][N:20]2[N:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[C:19]2[CH:18]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 168937Lithium hydroxide, monohydrateHCID 89635796HCID 89635796, compound

Product 1

HCID 89635780HCID 89635780, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1M aq. solution of LiOH.H2O (0.4 mL) was added to a stirred solution of ethyl 5-((2R,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate (Isomer-I) (Int-60) (0.07 g, 0.14 mmol) in EtOH (5 mL) and the stirring was continued at 90° C. for 8 h. The reaction mixture was concentrated under reduced pressure to afford the crude product. The crude product thus obtained was diluted with cold water, acidified with citric acid solution, filtered the solid precipitated to afford 5-((2R,4R)-2-(2,5-difluorophenyl)-4-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid (Int-62) as yellow solid. MS (ESI): m/z 360(M+H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford the crude product
  3. customThe crude product thus obtained
  4. filtrationfiltered the solid
  5. customprecipitated

Sources & evidence

ORD record
ord-59799336f71a4ad9b07dc4f12a7ec7ce
Source dataset
uspto-grants-2016_08
Patent number
US09402833B2

Reaction notes

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