Sodium Hydroxide → HCID 12993386, compound

HRID 1268084Notes

Reaction equation

HRID 1268084 reaction equation
[CH2:1]([N:8]([CH2:12][C:13]1[CH:14]=[C:15]([CH:33]=[CH:34][C:35]=1[OH:36])[O:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20]([NH:24][C:25](=[O:31])[C:26]([O:28]CC)=[O:27])=[CH:19][C:18]=1[CH3:32])[CH:9]([CH3:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1.O>[CH2:1]([N:8]([CH2:12][C:13]1[CH:14]=[C:15]([CH:33]=[CH:34][C:35]=1[OH:36])[O:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20]([NH:24][C:25](=[O:31])[C:26]([OH:28])=[O:27])=[CH:19][C:18]=1[CH3:32])[CH:9]([CH3:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12993383HCID 12993383, compound

Product 1

HCID 12993386HCID 12993386, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Ethyl {[4-(3-{[benzyl(isopropyl)amino]methyl}-4-hydroxyphenoxy)-3,5-dimethylphenyl]amino}(oxo)acetate (50 mg, 0,10 mmol) and NaOH (40 mg, 1.02 mmol) are dissolved in dioxane/water (0.5 1, 1:1 v/v) and stirred at room temperature for 1 h. The reaction mixture is partitioned between ethyl acetate and potassium dihydrogen phosphate/disodium hydrogen phosphate buffer solution (pH 7), and the organic phase is salted out with NaCl, filtered and evaporated. The resulting crude product is purified by preparative RP-HPLC with a water/acetonitrile/TFA eluent.

Workup

  1. customThe reaction mixture is partitioned between ethyl acetate and potassium dihydrogen phosphate/disodium hydrogen phosphate buffer solution (pH 7)
  2. filtrationfiltered
  3. customevaporated
  4. customThe resulting crude product is purified by preparative RP-HPLC with a water/acetonitrile/TFA eluent

Sources & evidence

ORD record
ord-2f7471f52d1441bea452b03d4f7ce32c
Source dataset
uspto-grants-2003_04
Patent number
US06555580B2

Reaction notes

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