Hydrochloric Acid → HCID 69429375, compound

HRID 1295289Notes

Reaction equation

HRID 1295289 reaction equation
[CH3:1][N:2]([C:24]1[S:25][C:26]([CH2:35][CH2:36][C:37]([O:39]C)=[O:38])=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:28]=1)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[N:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:15][C:16]=2[CH3:17])=[CH:6][CH:5]=1.[OH-].[Na+].O1CCCC1.[ClH:48]>O.CO>[ClH:48].[CH3:1][N:2]([C:24]1[S:25][C:26]([CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[C:27]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:28]=1)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[N:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:15][C:16]=2[CH3:17])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69428801HCID 69428801, compound

Product 1

HCID 69429375HCID 69429375, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 3-[2-[N-methyl-N-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]amino]-4-phenyl-5-thiazolyl]propionate (570 mg), 1N aqueous sodium hydroxide solution (2 ml), tetrahydrofuran (5 ml) and methanol (5 ml) was stirred at room temperature for 1 hr. The reaction mixture was poured into water, neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was dissolved in diethyl ether (40 ml) and 10% hydrochloric acid-methanol (0.5 ml) was added. The precipitated solid was collected by filtration and recrystallized from methanol-diethyl ether to give 3-[2-[N-methyl-N-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]amino]-4-phenyl-5-thiazolyl]propionic acid hydrochloride (270 mg, yield 46%) as colorless crystals. melting point: 106–108° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in diethyl ether (40 ml)
  6. addition10% hydrochloric acid-methanol (0.5 ml) was added
  7. filtrationThe precipitated solid was collected by filtration
  8. customrecrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-e9c66623d8e545cdb9f107e1fcc4a9d2
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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