Propanal → Methyl 3-[4-({3-[[(4-phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}oxy)phenyl]propanoate

HRID 732191Notes

Reaction equation

HRID 732191 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:12]=O)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:14][C:15]1[CH:16]=[C:17]([CH:32]=[CH:33][CH:34]=1)[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:49](=O)[CH2:50][CH3:51]>O.ClCCCl.C(O)(=O)C>[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][N:14]([CH2:49][CH2:50][CH3:51])[C:15]3[CH:16]=[C:17]([CH:32]=[CH:33][CH:34]=3)[CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:25]=3)[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 527PropanalHCID 35388144-Phenyl-1,3-thiazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23143302Methyl 3-{4-[(3-aminobenzyl)oxy]phenyl}-propanoate

Product 1

HCID 23143254Methyl 3-[4-({3-[[(4-phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}oxy)phenyl]propanoateYield 78.5%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a mixture of 4-phenyl-1,3-thiazole-2-carbaldehyde (210 mg, 1.1 mmol), methyl 3-{4-[(3-aminobenzyl)oxy]phenyl}-propanoate (285 mg, 1.0 mmol), acetic acid (0.2 mL) and 1,2-dichloroethane (5 mL) was added sodium triacetoxyborohydride (0.6 g, 2.8 mmol) under ice-cooling, and the mixture was warmed to room temperature and stirred for 1 hr. Propanal (200 mg, 3.4 mmol) was added to the reaction mixture, and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:2 in volume ratio) to give the title compound (393 mg, yield 78%) as a yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred at room temperature for 1 hr
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:2 in volume ratio)

Sources & evidence

ORD record
ord-fcf9313ff1bb41baac2c41f165c80b30
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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