Hydrochloric Acid → (2S)-(4-carboxythiazol-2-ylthio)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}acetamide

HRID 545107Notes

Reaction equation

HRID 545107 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH:13][C:14](=[O:27])[CH2:15][S:16][C:17]2[S:18][CH:19]=[C:20]([C:22]([O:24]CC)=[O:23])[N:21]=2)[CH2:7]1.[OH-].[Na+].Cl>CO.O1CCCC1>[C:22]([C:20]1[N:21]=[C:17]([S:16][CH2:15][C:14]([NH:13][CH2:12][C@@H:8]2[O:9][CH2:10][CH2:11][N:6]([CH2:5][C:4]3[CH:28]=[CH:29][C:30]([Cl:31])=[C:2]([Cl:1])[CH:3]=3)[CH2:7]2)=[O:27])[S:18][CH:19]=1)([OH:24])=[O:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67170480(2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-[4-(ethoxycarbonyl)thiazol-2-ylthio]acetamide

Product 1

HCID 59009100(2S)-(4-carboxythiazol-2-ylthio)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}acetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The resultant product (850 mg) of (1-4) was dissolved in methanol (4 mL) and tetrahydrofuran (4 mL), 1 mol/L aqueous sodium hydroxide solution (4 mL) was added, and the mixture was stirred overnight at room temperature. 1 mol/L hydrochloric acid was added to the reaction mixture, and the organic solvent alone was evaporated under reduced pressure. Saturated brine was added to the obtained residue, and the mixture was extracted with a mixed solvent of chloroform-methanol. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (479 mg) as a white solid.

Workup

  1. customthe organic solvent alone was evaporated under reduced pressure
  2. additionSaturated brine was added to the obtained residue
  3. extractionthe mixture was extracted with a mixed solvent of chloroform-methanol
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography
  7. customThe solvent was evaporated from the eluent

Sources & evidence

ORD record
ord-43090eff8a26462d896ed581fd8f0291
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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