Acetic Acid → HCID 57541930, compound

HRID 2422275Notes

Reaction equation

HRID 2422275 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([NH2:12])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13]([C:15]1[CH:34]=[CH:33][C:18]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)=O.C(O)(=O)C.C(=O)([O-])O.[Na+]>ClCCCl>[C:1]1([C:7]2[N:8]=[C:9]([NH:12][CH2:13][C:15]3[CH:34]=[CH:33][C:18]([CH2:19][O:20][C:21]4[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:23][CH:22]=4)=[CH:17][CH:16]=3)[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 403022-Amino-4-phenylthiazoleHCID 516892Sodium BicarbonateHCID 86626064HCID 86626064, compound

Product 1

HCID 57541930HCID 57541930, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-phenyl-1,3-thiazol-2-amine (0.25 g, 1.4 mmol), methyl 3-[4-[(4-formylbenzyl)oxy]phenyl]propionate (0.58 g, 2.0 mmol) and acetic acid (0.25 g, 4.2 mmol) in 1,2-dichloroethane (15 mL) was added triacetoxysodium borohydride (0.83 g, 3.9 mmol), and the mixture was stirred at room temperature for 2 days. The reaction mixture was poured into aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1) to give the title compound (0.31 g, yield 49%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-e9469580f0564903813ec15a61c6f042
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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