Hydrochloric Acid → 3-({[(3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]-decan-3-yl]carbonyl}amino)-propionic acid

HRID 1934748Notes

Reaction equation

HRID 1934748 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]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[S:12][CH2:11][C@H:10]1[C:29]([NH:31][CH2:32][CH2:33][C:34]([O:36]CC1C=CC=CC=1)=[O:35])=[O:30])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(OCC)(=O)C.Cl>C(O)C>[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]([CH:26]([CH3:28])[CH3:27])=[CH:24][CH:25]=3)[CH2:17][CH2:18]2)[S:12][CH2:11][C@H:10]1[C:29]([NH:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[O:30])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 70156809benzyl 3-{[(3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decan-3-yl]carbonyl}amino-propionate

Product 1

HCID 187388023-({[(3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]-decan-3-yl]carbonyl}amino)-propionic acidYield 92.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 8 ml of ethanol was dissolved 0.38 g of benzyl 3-({[(3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decan-3-yl]carbonyl}amino)-propionate. Then, 1.90 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 4 hours. The reaction mixture was poured into a mixture of ice water and ethyl acetate, and the aqueous layer was separated. Ethyl acetate was added to the aqueous layer thus obtained, pH was adjusted to 2.0 with 2 mol/L hydrochloric acid, and the organic layer was separated. The organic layer thus obtained 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. Thus, 0.30 g of 3-({[(3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]-decan-3-yl]carbonyl}amino)-propionic acid was obtained as a colorless oily product.

Workup

  1. customthe aqueous layer was separated
  2. additionEthyl acetate was added to the aqueous layer
  3. customthus obtained
  4. customthe organic layer was separated
  5. customThe organic layer thus obtained
  6. washwas 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

Sources & evidence

ORD record
ord-1d4b4b780d8f42aba9cfd50b185bfb22
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

Loading…