Hydrochloric Acid → 5-(Carboxymethyl)-3-[3-(cyclopentyloxy)-4-methoxyphenyl]-4,5-dihydroisoxazole-5-carboxylic acid

HRID 1169849Notes

Reaction equation

HRID 1169849 reaction equation
C[O:2][C:3]([C:5]1([CH2:24][C:25]([O:27]C)=[O:26])[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:11]=2)[CH2:6]1)=[O:4].O1CCCC1.[OH-].[Li+].Cl>O>[C:25]([CH2:24][C:5]1([C:3]([OH:4])=[O:2])[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[CH:11]=2)[CH2:6]1)([OH:27])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 686864923-(3-Cyclopentyloxy-4-methoxy-phenyl)-5-methoxy carbonylmethyl-4,5-dihydro-isoxazol-5-carboxylic Acid Methyl Ester

Product 1

HCID 595509785-(Carboxymethyl)-3-[3-(cyclopentyloxy)-4-methoxyphenyl]-4,5-dihydroisoxazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of the compound obtained from step c in tetrahydrofuran (1.0 eq), was added and lithium hydroxide (5.0 eq) in water (as 5N solution). The mixture was stirred at room temperature over night. The solvent was removed under reduced pressure and the residue thus obtained was diluted with water and acidified with drops of concentrated hydrochloric acid. The organic compound was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulphate and finally concentrated under reduced pressure to afford title organic compound.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue thus obtained
  3. extractionThe organic compound was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationfinally concentrated under reduced pressure
  7. customto afford title organic compound

Sources & evidence

ORD record
ord-7781ad8aba524c7b94bd22e429429659
Source dataset
uspto-grants-2010_11
Patent number
US07825147B2

Reaction notes

Loading…