Ethyl Acetate → HCID 11740793, compound

HRID 2355002Notes

Reaction equation

HRID 2355002 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[C:21]([C:23](=[O:30])[NH:24][C:25]3[S:26][CH:27]=[CH:28][N:29]=3)[CH:20]=[C:19]([O:31][CH:32]([CH3:34])[CH3:33])[CH:18]=2)=[N:12][CH:11]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>O1CCCC1>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[C:21]([CH:20]=[C:19]([O:31][CH:32]([CH3:34])[CH3:33])[CH:18]=2)[C:23]([NH:24][C:25]2[S:26][CH:27]=[CH:28][N:29]=2)=[O:30])=[N:12][CH:11]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 10431879HCID 10431879, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11740793HCID 11740793, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

After adding 6.0 mg (0.16 mmol) of lithium aluminum hydride to a solution of 60.0 mg (0.15 mmol) of the 6-[3-isopropoxy-5-(thiazol-2-ylcarbamoyl)-phenoxy]-nicotinic acid methyl ester obtained in Production Example 65 in tetrahydrofuran (5.0 ml) while cooling on ice, the mixture was stirred at 0° C. for 1 hour. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture, extraction was performed with ethyl acetate, and the organic layer was dried and then concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (chloroform:methanol=30:1) to obtain the title compound as a white solid. The analysis data for the compound obtained in Production Example 66 are shown below.

Workup

  1. temperaturewhile cooling on ice
  2. customthe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-82a3651765ba4cd6a5ef4e5f26eec42d
Source dataset
uspto-grants-2010_07
Patent number
US07754743B2

Reaction notes

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