4-Chlorobenzaldehyde → (2S)-N-{[4-(4-chlorobenzyl)morpholin-2-yl]methyl}-[4-(ethoxycarbonylmethyl)thiazol-2-ylthio]acetamide

HRID 545119Notes

Reaction equation

HRID 545119 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1[N:8]=[C:9]([S:12][CH2:13][C:14]([NH:16][CH2:17][C@H:18]2[O:23][CH2:22][CH2:21][NH:20][CH2:19]2)=[O:15])[S:10][CH:11]=1)=[O:5])[CH3:2].[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(O)(=O)C>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][N:20]2[CH2:21][CH2:22][O:23][C@@H:18]([CH2:17][NH:16][C:14](=[O:15])[CH2:13][S:12][C:9]3[S:10][CH:11]=[C:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:8]=3)[CH2:19]2)=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67169399(2S)-[4-(ethoxycarbonylmethyl)thiazol-2-ylthio]-N-[(morpholin-2-yl)methyl]acetamide

Product 1

HCID 67168675(2S)-N-{[4-(4-chlorobenzyl)morpholin-2-yl]methyl}-[4-(ethoxycarbonylmethyl)thiazol-2-ylthio]acetamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

The resultant product (899 mg) of (75-3) was dissolved in methylene chloride (12.5 mL), 4-chlorobenzaldehyde (387 mg) and acetic acid (143 μL) were added and the mixture was stirred at room temperature for 1 hr. Sodium triacetoxyborohydride (1.06 g) was added to the reaction mixture and the mixture was further stirred overnight at room temperature. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with chloroform. The extract was washed with saturated brine, 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 acetone as an eluent. The solvent was evaporated from the eluent to give the title compound (1.16 g) as a pale-yellow oil.

Workup

  1. stirringthe mixture was further stirred overnight at room temperature
  2. extractionthe mixture was extracted with chloroform
  3. washThe extract was washed with saturated brine
  4. dry with materialdried 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-6464a96edfe248a3a7c502dcc3623a65
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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