Tetrahydrofuran → 1-{[6-(2-Methylcarbamoyl-pyridin-4-yloxy)-benzooxazol-2-ylamino]-methyl}-cyclohexanecarboxylic acid

HRID 1988406Notes

Reaction equation

HRID 1988406 reaction equation
C([O:3][C:4]([C:6]1([CH2:12][NH:13][C:14]2[O:15][C:16]3[CH:22]=[C:21]([O:23][C:24]4[CH:29]=[CH:28][N:27]=[C:26]([C:30](=[O:33])[NH:31][CH3:32])[CH:25]=4)[CH:20]=[CH:19][C:17]=3[N:18]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].C1COCC1>CO>[CH3:32][NH:31][C:30]([C:26]1[CH:25]=[C:24]([O:23][C:21]2[CH:20]=[CH:19][C:17]3[N:18]=[C:14]([NH:13][CH2:12][C:6]4([C:4]([OH:5])=[O:3])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]4)[O:15][C:16]=3[CH:22]=2)[CH:29]=[CH:28][N:27]=1)=[O:33]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 248210661-{[6-(2-Methylcarbamoyl-pyridin-4-yloxy)-benzooxazol-2-ylamino]methyl}-cyclohexanecarboxylic acid ethyl ester

Product 1

HCID 248213051-{[6-(2-Methylcarbamoyl-pyridin-4-yloxy)-benzooxazol-2-ylamino]-methyl}-cyclohexanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-{[6-(2-Methylcarbamoyl-pyridin-4-yloxy)-benzooxazol-2-ylamino]methyl}-cyclohexanecarboxylic acid ethyl ester (1 eq) was dissolved in 3 M sodium hydroxide (20 eq); THF and methanol were added to homogenize the solution. The mixture was allowed to react at room temperature overnight. The solvents were removed. The crude product was brought to a pH of 4 with 1 N HCl, then to pH of 7 with saturated aqueous sodium bicarbonate. This solution was saturated with solid sodium chloride then extracted three times with ethyl acetate. The combined organic extracts were washed once with brine, dried with anhydrous sodium sulfate, filtered and concentrated. The product was purified by silica gel column in isopropanol and dichloromethane (50%) MH+=425.1.

Workup

  1. customto react at room temperature overnight
  2. customThe solvents were removed
  3. extractionthen extracted three times with ethyl acetate
  4. washThe combined organic extracts were washed once with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by silica gel column in isopropanol

Sources & evidence

ORD record
ord-8381460954a14e019d31b1cb9087a856
Source dataset
uspto-grants-2009_06
Patent number
US07553854B2

Reaction notes

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