Hydrochloric Acid → HCID 11037455, compound

HRID 584443Notes

Reaction equation

HRID 584443 reaction equation
[OH-].[Na+].[CH3:3][N:4]([C:30]1[N:35]=[CH:34][CH:33]=[CH:32][N:31]=1)[CH2:5][CH2:6][O:7][C:8]1[CH:29]=[CH:28][C:11]([CH2:12][O:13]/[N:14]=[C:15](/[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)\[CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[CH:10][CH:9]=1.CO.Cl>O1CCCC1>[CH3:3][N:4]([C:30]1[N:31]=[CH:32][CH:33]=[CH:34][N:35]=1)[CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][O:13]/[N:14]=[C:15](/[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)\[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 11113113HCID 11113113, compound

Product 1

HCID 11037455HCID 11037455, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1N aqueous saturated solution of sodium hydroxide (5 ml) was added to a solution of methyl E-4-[4-[2-(methyl-2-pyrimidylamino)ethoxy]benzyloxyimino]-4-phenylbutyrate (1.22 g) in tetrahydrofuran (10 ml)-methanol (5 ml) and stirred at room temperature for 1 hour. 1N hydrochloric acid (5 ml) was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was recrystallized from ethyl acetate-hexane to obtain E-4-[4-[2-(methyl-2-pyrimidylamino)ethoxy]benzyloxyimino]-4-phenylbutyric acid (1.09 g, yield 92%) as colorless crystals. m.p. 72-73° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0b2cc31786ea49cf92f724c8b5c58d15
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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