Lithium Hydroxide → HCID 58465352, compound

HRID 521348Notes

Reaction equation

HRID 521348 reaction equation
[OH-].[Li+].[CH3:3][C@H:4]1[C:12]2[C:11]([C:13]3[S:17][C:16]([C:18]([O-:20])=[O:19])=[CH:15][CH:14]=3)=[N:10][CH:9]=[N:8][C:7]=2[C@H:6]([O:21]C(=O)C2C=CC([N+]([O-])=O)=CC=2)[CH2:5]1>C1COCC1.O>[OH:21][C@H:6]1[C:7]2[N:8]=[CH:9][N:10]=[C:11]([C:13]3[S:17][C:16]([C:18]([OH:20])=[O:19])=[CH:15][CH:14]=3)[C:12]=2[C@H:4]([CH3:3])[CH2:5]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67436393HCID 67436393, compound

Product 1

HCID 58465352HCID 58465352, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (6 mg, 0.146 mmol) was added to a solution of 5-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)thiophene-2-carboxylate (32 mg, 0.073 mmol) in THF (0.5 mL) and water (0.5 mL). The reaction mixture was stirred at room temperature for 1 hour. LC-MS of the reaction mixture showed no more starting material. THF was removed under reduced pressure, and 1N HCl (5 mL) was added. The reaction mixture was extracted with EtOAc (3×5 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give 5-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)thiophene-2-carboxylic acid. The crude mixture was used directly in the next step without further purification.

Workup

  1. customTHF was removed under reduced pressure, and 1N HCl (5 mL)
  2. additionwas added
  3. extractionThe reaction mixture was extracted with EtOAc (3×5 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-22ce1c998df144e3a906157c0350e369
Source dataset
uspto-grants-2016_05
Patent number
US09328091B2

Reaction notes

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