Ethanol → ethyl (3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decane-3-carboxylate

HRID 1934744Notes

Reaction equation

HRID 1934744 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]([OH:31])=[O:30])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:32](O)[CH3:33].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[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]([CH3:27])[CH3:28])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[S:12][CH2:11][C@H:10]1[C:29]([O:31][CH2:32][CH3:33])=[O:30])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 70154971(3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decane-3-carboxylic acid

Product 1

HCID 86758062ethyl (3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 56 ml of methylene chloride was dissolved 2.80 g of (3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decane-3-carboxylic acid, to which were successively added at 0-5° C. 0.56 ml of ethanol, 0.16 g of N,N-dimethylaminopyridine and 1.98 g of dicyclohexyl carbodiimide. After stirring the mixture at ambient temperature for 24 hours, the insoluble matter was filtered off. The filtrate was poured into ice water, 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, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by column chromatography [eluent: toluene:ethyl acetate=50:1] gave 0.85 g of ethyl (3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decane-3-carboxylate as a colorless oily product.

Workup

  1. additionto which were successively added at 0-5° C
  2. filtrationthe insoluble matter was filtered off
  3. additionThe filtrate was poured into ice water, pH
  4. customthe organic layer was separated
  5. customThe organic layer thus obtained
  6. washwas washed successively with water, saturated aqueous solution of sodium hydrogen carbonate 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. customPurification of the residue by column chromatography [eluent: toluene:ethyl acetate=50:1]

Sources & evidence

ORD record
ord-4517a7ace4d649048042927a2bf8773e
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

Loading…