Water → 3-[4-[[4-[[(2-Phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzyl]oxy]phenyl]propanoic acid (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester

HRID 732219Notes

Reaction equation

HRID 732219 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]([CH2:21][C:22]2[CH:40]=[CH:39][C:25]([CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)[C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:42][C:43]1[O:44][C:45](=[O:49])[O:46][C:47]=1[CH3:48].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:48][C:47]1[O:46][C:45](=[O:49])[O:44][C:43]=1[CH2:42][O:37][C:36](=[O:38])[CH2:35][CH2:34][C:31]1[CH:30]=[CH:29][C:28]([O:27][CH2:26][C:25]2[CH:24]=[CH:23][C:22]([CH2:21][N:9]([CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:10]3[S:11][CH:12]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:14]=3)=[CH:40][CH:39]=2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 98555184-(Chloromethyl)-5-methyl-1,3-dioxol-2-oneHCID 111688073-[4-[[4-[[(2-Phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzyl]oxy]phenyl]propanoic acid

Product 1

HCID 578379273-[4-[[4-[[(2-Phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzyl]oxy]phenyl]propanoic acid (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl esterYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[4-[[4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzyl]oxy]phenyl]propanoic acid (450 mg, 0.82 mmol), 4-(chloromethyl)-5-methyl-1,3-dioxol-2-one (146 mg, 0.99 mmol) and potassium carbonate (170 mg, 1.23 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 5 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (175 mg, yield 32%) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-440110e4ea33468f95f3ebe8ec9c401a
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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