Citric Acid → HCID 89635780, compound

HRID 2167738Notes

Reaction equation

HRID 2167738 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-24084f957af24126960f21cc5fdeb3ea
Source dataset
uspto-grants-2015_06
Patent number
US09045478B2

Reaction notes

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