Hydrochloric Acid → HCID 18738805, compound

HRID 1934749Notes

Reaction equation

HRID 1934749 reaction equation
[C:1]([N:9]1[C:13]2([CH2:18][CH2:17][CH:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([O:28]C)=[O:27])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[S:12][CH2:11][C@H:10]1[C:30]([OH:32])=[O:31])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[C:1]([N:9]1[C:13]2([CH2:14][CH2:15][CH:16]([O:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]([OH:28])=[O:27])=[CH:24][CH:25]=3)[CH2:17][CH2:18]2)[S:12][CH2:11][C@H:10]1[C:30]([OH:32])=[O:31])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70156381HCID 70156381, compound

Product 1

HCID 18738805HCID 18738805, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 4 ml of methanol was suspended 0.40 g of (3R)-4-benzoyl-8-[4-(methoxycarbonyl)phenoxy]-1-thia-4-azaspiro[4.5]decane-3-carboxylic acid. After adding thereto 4.40 ml of 1 mol/L aqueous solution of sodium hydroxide at 0-5° C., the resulting mixture was stirred at ambient temperature for 6 hours. The reaction mixture was poured into ice water, pH was adjusted to 2.0 with 2 mol/L hydrochloric acid, and then the product was extracted with ethyl acetate. 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. Ethyl ether and ethyl acetate was added to the residue, and the deposited crystal was collected by filtration to obtain 0.30 g of (3R)-4-benzoyl-8-(4-carboxyphenoxy)-1-thia-4-azaspiro[4.5]-decane-3-carboxylic acid as a colorless crystalline product.

Workup

  1. additionAfter adding
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionEthyl ether and ethyl acetate was added to the residue
  7. filtrationthe deposited crystal was collected by filtration

Sources & evidence

ORD record
ord-19ebb2650de04e59a5350411d5732e6c
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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