Lithium Hydroxide → HCID 69848379, compound

HRID 352177Notes

Reaction equation

HRID 352177 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]2[CH2:23][CH2:24][C:25]([O:27]C)=[O:26])=[O:15])=[C:12]([CH3:29])[O:11][N:10]=1.[Li+].[OH-]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([NH:16][C@@H:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]2[CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:15])=[C:12]([CH3:29])[O:11][N:10]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 22714062HCID 22714062, compound

Product 1

HCID 69848379HCID 69848379, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-(2-{[3-(2-chloro-6-fluorophenyl)-5-methylisoxazol-4-yl]carbonylamino}cyclohexyl)propanoate (0.127 g, 0.3 mmol) in THF (5 mL) was treated with a 0.5 M sol'n of LiOH in water (3 mL). The sol'n was stirred at r.t. for 5 hr. The reaction was diluted with water (3 mL) and washed with EtOAc (2×5 mL). The pH of the aqueous was adjusted to ˜3 with 0.1 M HCl and extracted with EtOAc (4×5 mL). The organic extractions were then washed with brine (2×5 mL), dried over sodium sulfate and the solvent removed to afford 0.095 g (80%) as a white solid. MS (ES+) m/z 409.0 (M+H)+, (ES−) m/z 407.0 (M−H)−.

Workup

  1. washwashed with EtOAc (2×5 mL)
  2. extractionextracted with EtOAc (4×5 mL)
  3. extractionThe organic extractions
  4. washwere then washed with brine (2×5 mL)
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed
  7. customto afford 0.095 g (80%) as a white solid

Sources & evidence

ORD record
ord-a6b66fd4dd0440619e7773a938433b7e
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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