Hydrochloric Acid → HCID 22467109, compound

HRID 1934757Notes

Reaction equation

HRID 1934757 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][CH:6]1[C:10](=[O:11])[N:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2([CH2:24][CH2:23][N:22]([CH2:25][CH2:26][C:27](=O)[C:28]([O:30]CC)=[O:29])[CH2:21][CH2:20]2)[S:7]1)C.[OH-].[Na+].C(OCC)(=[O:39])C.Cl>C(O)C>[C:4]([CH2:5][CH:6]1[C:10](=[O:11])[N:9]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2([CH2:24][CH2:23][N:22]([C:25](=[O:39])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH2:21][CH2:20]2)[S:7]1)([OH:3])=[O:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 22467121HCID 22467121, compound

Product 1

HCID 22467109HCID 22467109, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 2.5 ml of ethanol was dissolved 0.51 g of ethyl 4-[2-(2-ethoxy-2-oxoethyl)-3-oxo-4-phenethyl-1-thia-4,8-diazaspiro[4.5]decan-8-yl]-oxobutanoate. After adding 2.5 ml of 1 mol/L aqueous solution of sodium hydroxide at 0-5° C., the resulting mixture was stirred at ambient temperature for 1.5 hours. The reaction mixture was poured into a mixture of ice water and ethyl acetate, 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, 0.34 g of 4-[2-(carboxymethyl)-3-oxo-4-phenethyl-1-thia-4,8-diazaspiro[4.5]decan-8-yl]-4-oxobutanoic acid was obtained as a yellow oily product.

Workup

  1. customthe organic layer was separated
  2. customThe organic layer thus obtained
  3. washwas 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

Sources & evidence

ORD record
ord-7b9b8dabce2140558fb4cbb6e0c2d32a
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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