Lithium hydroxide, monohydrate → HCID 11778835, compound

HRID 2054120Notes

Reaction equation

HRID 2054120 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]2([C:21]([O:23]CC)=[O:22])[O:15][N:14]=[C:13]([C:16]([O:18]CC)=[O:17])[CH2:12]2)=[CH:2]1.O.[OH-].[Li+]>C(O)C.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]2([C:21]([OH:23])=[O:22])[O:15][N:14]=[C:13]([C:16]([OH:18])=[O:17])[CH2:12]2)=[CH:2]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 12084225HCID 12084225, compound

Product 1

HCID 11778835HCID 11778835, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.03 g (3.0 mmols) of diethyl 5-(RS)-(3-indolylmethyl)-4,5-dihydroisoxazole-3,5-dicarboxylate was dissolved in a mixed solvent of 16 ml of ethanol and 4 ml of water. 290 mg (6.9 mmols) of lithium hydroxide monohydrate was added thereto, and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated to a volume of ⅓ or so under reduced pressure, and 15 ml of water and 1N hydrochloric acid were added to adjust the reaction solution to a pH of from 1 to 2. The resulting solution was extracted three times with 20 ml of ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The anhydrous magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to obtain 5-(RS)-(3-indolylmethyl)-4,5-dihydroisoxazole-3,5-dicarboxylic acid as a light yellow powder.

Workup

  1. concentrationThe reaction solution was concentrated to a volume of ⅓ or so under reduced pressure, and 15 ml of water and 1N hydrochloric acid
  2. additionwere added
  3. extractionThe resulting solution was extracted three times with 20 ml of ethyl acetate
  4. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe anhydrous magnesium sulfate was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7861eefceaa04483a39d1d91d5a11a9a
Source dataset
uspto-grants-2008_02
Patent number
US07329427B2

Reaction notes

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