Acetic Acid → N-(6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-(2-hydroxy-2-methylpropanoyl)furo[2,3-b]pyridin-3-yl)-2-hydroxyacetamide

HRID 8816Notes

Reaction equation

HRID 8816 reaction equation
[OH-].[Li+].O.C([O:7][CH2:8][C:9]([NH:11][C:12]1[C:20]2[C:15](=[N:16][C:17]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])=[C:18]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH:19]=2)[O:14][C:13]=1[C:35](=[O:40])[C:36]([OH:39])([CH3:38])[CH3:37])=[O:10])(=O)C.CO.C(O)(=O)C>C1COCC1>[Cl:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:17]1[N:16]=[C:15]2[O:14][C:13]([C:35](=[O:40])[C:36]([OH:39])([CH3:38])[CH3:37])=[C:12]([NH:11][C:9](=[O:10])[CH2:8][OH:7])[C:20]2=[CH:19][C:18]=1[C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 219849132-{[6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(2-hydroxy-2-methylpropanoyl)furo[2,3-b]pyridin-3yl]amino}-2-oxoethyl acetate

Product 1

HCID 10028888N-(6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-(2-hydroxy-2-methylpropanoyl)furo[2,3-b]pyridin-3-yl)-2-hydroxyacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide-H2O (0.293 g), the product of Step A (3.78 g), and methanol (8.4 mL) were combined in 245 mL of THF and stirred at room temperature. After 5 min 0.50 mL of acetic acid was added and the solution concentrated. The residue was diluted with ethyl acetate and this solution washed two times with aqueous sodium bicarbonate. The solution was concentrated and purified via flash chromatography on silica gel with a gradient elution of 0 to 55% ethyl acetate in methylene chloride. The product was then further purified by recrystallization from ethanol to afford the title compound. HPLC/MS: 499.0 (M+1), 500.8 (M+3); Rt=3.77 min.

Workup

  1. concentrationthe solution concentrated
  2. additionThe residue was diluted with ethyl acetate
  3. washthis solution washed two times with aqueous sodium bicarbonate
  4. concentrationThe solution was concentrated
  5. custompurified via flash chromatography on silica gel with a gradient elution of 0 to 55% ethyl acetate in methylene chloride
  6. customThe product was then further purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-2587e99f20af4b9a95cc53879079e3af
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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