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

HRID 8801Notes

Reaction equation

HRID 8801 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][C:31]([Cl:34])=[CH:30][C:29]=3[Cl:35])=[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:36](=[O:41])[C:37]([OH:40])([CH3:39])[CH3:38])=[O:10])(=O)C.CO>C1COCC1>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:18]2[CH:19]=[C:20]3[C:12]([NH:11][C:9](=[O:10])[CH2:8][OH:7])=[C:13]([C:36](=[O:41])[C:37]([OH:40])([CH3:38])[CH3:39])[O:14][C:15]3=[N:16][C:17]=2[C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 219849022-{[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2-hydroxy-2-methylpropanoyl)furo[2,3-b]pyridin-3-yl]amino}-2-oxoethyl acetate

Product 1

HCID 10052826N-(5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2-hydroxy-2-methylpropanoyl)furo[2,3-b]pyridin-3-yl)-2-hydroxyacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide-H2O (0.004 g; 0.174 mmol), the product of Step C (0.100 g; 0.174 mmol), and methanol (0.3 mL) were combined in 2 mL of THF and stirred at room temperature. The reaction was monitored by TLC until complete at which point the reaction was quenched by addition of 0.50 mL of acetic acid. The reaction was diluted with ethyl acetate and then washed two times with aqueous sodium bicarbonate. The solution was concentrated and purified via MPLC chromatography on silica gel with a gradient elution of 0 to 50% ethyl acetate/hexanes. The product was further purified by recrystallization from ethanol to afford the title compound. HPLC/MS 534.8 (M+2); Rt=4.09 min.

Workup

  1. customwas quenched by addition of 0.50 mL of acetic acid
  2. additionThe reaction was diluted with ethyl acetate
  3. washwashed two times with aqueous sodium bicarbonate
  4. concentrationThe solution was concentrated
  5. custompurified via MPLC chromatography on silica gel with a gradient elution of 0 to 50% ethyl acetate/hexanes
  6. customThe product was further purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-1d44fccaefc041d68a448a30ecfbc9e3
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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