Hydrochloric Acid → HCID 69216837, compound

HRID 2222024Notes

Reaction equation

HRID 2222024 reaction equation
C([O:9][CH2:10][C:11]1[S:12][CH:13]=[C:14](/[CH:16]=[CH:17]/[C:18]2[C:19]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]4[N:40]=[C:41]([C:45]5[CH:50]=[CH:49][C:48]([CH2:51][C:52]([O:54]CC)=[O:53])=[CH:47][CH:46]=5)[O:42][C:43]=4[CH3:44])=[C:33]([O:57][CH3:58])[CH:32]=3)=[N:20][N:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:22]=2)[N:15]=1)(=O)C1C=CC=CC=1.O1CCCC1.[OH-].[Na+].Cl>O.C(O)C>[OH:9][CH2:10][C:11]1[S:12][CH:13]=[C:14](/[CH:16]=[CH:17]/[C:18]2[C:19]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]4[N:40]=[C:41]([C:45]5[CH:46]=[CH:47][C:48]([CH2:51][C:52]([OH:54])=[O:53])=[CH:49][CH:50]=5)[O:42][C:43]=4[CH3:44])=[C:33]([O:57][CH3:58])[CH:32]=3)=[N:20][N:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:22]=2)[N:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69218219HCID 69218219, compound

Product 1

HCID 69216837HCID 69216837, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of {4-[(E)-2-(3-{[4-({2-[4-(2-ethoxy-2-oxoethyl)phenyl]-5-methyl-1,3-oxazol-4-yl}methoxy)-3-methoxybenzyl]oxy}-1-phenyl-1H-pyrazol-4-yl)ethenyl]-1,3-thiazol-2-yl}methyl benzoate (0.5 g), tetrahydrofuran (6 mL) and ethanol (3 mL) was added 1N aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at 50° C. for 20 hrs. To the reaction mixture were added 1N hydrochloric acid (3 mL) and water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give (4-{4-[(4-{[(4-{(E)-2-[2-(hydroxymethyl)-1,3-thiazol-4-yl]ethenyl}-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}phenyl)acetic acid as crystals (0.4 g, yield 90%). Recrystallization twice from tetrahydrofuran-hexane gave colorless prism crystals. melting point: 204-205° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-673aea8e87e8491db780878081c0e130
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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