Ethanol → HCID 70154815, compound

HRID 1934745Notes

Reaction equation

HRID 1934745 reaction equation
C(O)C.O1CCCC1.[C:9]([N:17]1[C:21]2([CH2:26][CH2:25][CH:24]([C:27]([O:29]CC)=[O:28])[CH2:23][CH2:22]2)[S:20][CH2:19][C@H:18]1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>C(OCC)(=O)C.O>[C:9]([N:17]1[C:21]2([CH2:22][CH2:23][CH:24]([C:27]([OH:29])=[O:28])[CH2:25][CH2:26]2)[S:20][CH2:19][C@H:18]1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])(=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86758063HCID 86758063, compound

Product 1

HCID 70154815HCID 70154815, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a mixture consisting of 23 ml of ethanol and 23 ml of tetrahydrofuran was dissolved 2.30 g of ethyl (3R)-4-benzoyl-3-(tert-butoxycarbonyl)-1-thia-4-azaspiro[4.5]decane-8-carboxylate. Then, 15.9 ml of 1 mol/L aqueous solution of sodium hydroxide was added at 0-5° C. and the resulting mixture was stirred at ambient temperature for 2 hours. The solvent was distilled off under reduced pressure, the residue thus obtained was added to a mixture of water and ethyl acetate, and the aqueous layer was separated. Ethyl acetate was added to the aqueous layer, pH was adjusted to 2.0 with 2 mol/L hydrochloric acid, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Isopropyl ether was added to the residue and the deposited crystal was collected by filtration. Thus, 1.78 g of (3R)-4-benzoyl-3-(tert-butoxycarbonyl)-1-thia-4-azaspiro[4.5]decane-8-carboxylic acid was obtained as a colorless crystalline product.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue thus obtained
  3. customthe aqueous layer was separated
  4. additionEthyl acetate was added to the aqueous layer, pH
  5. customthe organic layer was separated
  6. washThe organic layer was washed successively with water and saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. additionIsopropyl ether was added to the residue
  10. filtrationthe deposited crystal was collected by filtration

Sources & evidence

ORD record
ord-931fe3be65f94959bfc2cdc40ddd1ed2
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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