Hydrochloric Acid → 3-[4-[[4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyl]sulfanyl]phenyl]propionic acid

HRID 1294294Notes

Reaction equation

HRID 1294294 reaction equation
Cl[CH2:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.[SH:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:26][CH:25]=1.C(N(CC)CC)C.Cl>O.CN(C)C=O>[CH3:14][C:13]1[O:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:10][C:9]=1[CH2:8][O:7][C:6]1[CH:21]=[CH:22][C:3]([CH2:2][S:23][C:24]2[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:28][CH:29]=2)=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 5797844-Mercaptohydrocinnamic AcidHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole

Product 1

HCID 688845593-[4-[[4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyl]sulfanyl]phenyl]propionic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (1.73 g), 3-(4-mercaptophenyl)propionic acid (1.00 g), triethylamine (1.22 g) and N,N-dimethylformamide (20 mL) was stirred at room temperature for 2 hrs. The reaction mixture was poured into water, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated to give crystals of 3-[4-[[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyl]sulfanyl]phenyl]propionic acid. Recrystallization from ethyl acetate gave colorless prism crystals (1.85 g, 73%). melting point: 157-158° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a3eea87b9f6f49dfae639f1839b55d64
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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