Sodium Hydroxide → HCID 23125723, compound

HRID 1820918Notes

Reaction equation

HRID 1820918 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]3[CH:29]=[CH:28][CH:27]=[CH:26][C:14]=3[C:15]=2[NH:16][C:17](=[O:25])[CH2:18][CH2:19][CH2:20][C:21]([O:23]C)=[O:22])=[O:10])=[N:6][CH:7]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]3[CH:29]=[CH:28][CH:27]=[CH:26][C:14]=3[C:15]=2[NH:16][C:17](=[O:25])[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23125711Methyl 5-[(2-{[(5-chloropyridin-2-yl)amino]carbonyl}benzofuran-3-yl)amino]-5-oxopentanoate

Product 1

HCID 23125723HCID 23125723, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-[(2-{[(5-chloropyridin-2-yl)amino]-carbonyl}benzofuran-3-yl)amino]-5-oxopentanoate (4.44 g) obtained in Example 9(1) is suspended in methanol (50 ml), and thereto is added 2N aqueous sodium hydroxide solution (30 ml) under ice-cooling followed by stirring at room temperature for 2 hours. After evaporating methanol under reduced pressure, the residue is diluted with water and washed with diethyl ether. The separated aqueous layer is acidified with 10% hydrochloric acid under ice-cooling, and the precipitates are collected by filtration. The resulting solid materials are washed successively with water, ethanol and diethyl ether, and dried to give the title compound (3.99 g). ESI-MS M/Z:400/402[M−H]−

Workup

  1. temperaturecooling
  2. customAfter evaporating methanol under reduced pressure
  3. additionthe residue is diluted with water
  4. washwashed with diethyl ether
  5. temperaturecooling
  6. filtrationthe precipitates are collected by filtration
  7. washThe resulting solid materials are washed successively with water, ethanol and diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-a19b84f33c104d7b8312e2399a3fb4d0
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

Loading…