Hydrochloric Acid → 3-[2-[N-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-N-(1-propyl)amino]-4-phenyl-5-thiazolyl]propionic acid hydrochloride

HRID 1295291Notes

Reaction equation

HRID 1295291 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:42]=[CH:41][C:18]([CH2:19][N:20]([C:24]2[S:25][C:26]([CH2:35][CH2:36][C:37]([O:39]C)=[O:38])=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:28]=2)[CH2:21][CH2:22][CH3:23])=[CH:17][CH:16]=1.O.[OH-].[Li+].O1CCCC1.[ClH:51]>CO.O>[ClH:51].[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:42]=[CH:41][C:18]([CH2:19][N:20]([C:24]2[S:25][C:26]([CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:28]=2)[CH2:21][CH2:22][CH3:23])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69430779methyl 3-[2-[N-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-N-(1-propyl)amino]-4-phenyl-5-thiazolyl]propionate

Product 1

HCID 694258363-[2-[N-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-N-(1-propyl)amino]-4-phenyl-5-thiazolyl]propionic acid hydrochlorideYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 3-[2-[N-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-N-(1-propyl)amino]-4-phenyl-5-thiazolyl]propionate (537 mg), lithium hydroxide hydrate (116 mg), tetrahydrofuran (6 ml), water (4 ml) and methanol (4 ml) was stirred at room temperature for 2 hrs. 1N Hydrochloric acid (2.8 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. A mixture of the obtained colorless oil, 10% hydrochloric acid-methanol (3 ml) and diethyl ether (30 ml) was stirred at room temperature for 10 min. and concentrated to give 3-[2-[N-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-N-(1-propyl)amino]-4-phenyl-5-thiazolyl]propionic acid hydrochloride (576 mg, yield 97%) as a colorless amorphous form.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. additionA mixture of the obtained colorless oil, 10% hydrochloric acid-methanol (3 ml) and diethyl ether (30 ml)
  6. stirringwas stirred at room temperature for 10 min.
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e1c23dfeb3c44ef5ba71e626676edaee
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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