Acetic Acid → HCID 10116033, compound

HRID 1838221Notes

Reaction equation

HRID 1838221 reaction equation
[C:1](O)(=O)[CH3:2].[C:5](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:19][C:20]1[CH:45]=[CH:44][C:23]([CH2:24][N:25]2[C:33]3[C:28](=[CH:29][C:30]([Cl:34])=[CH:31][CH:32]=3)[C:27]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:42])([CH3:35])[C:26]2=[O:43])=[C:22]([O:46][CH3:47])[CH:21]=1.C(=O)([O-])O.[Na+]>ClCCCl.CC(C)=O>[Cl:34][C:30]1[CH:29]=[C:28]2[C:33](=[CH:32][CH:31]=1)[N:25]([CH2:24][C:23]1[CH:44]=[CH:45][C:20]([NH:19][CH:1]([CH3:2])[CH3:5])=[CH:21][C:22]=1[O:46][CH3:47])[C:26](=[O:43])[C:27]2([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[Cl:42])[CH3:35]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15521770HCID 15521770, compound

Product 1

HCID 10116033HCID 10116033, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 180AcetoneSolvent

Procedure

0.26 ml of acetic acid, 0.14 ml of acetone and then 0.56 g of sodium triacetoxyborohydride are added to 0.40 g of the compound of Example 48 in 10 ml of 1,2-dichloroethane at room temperature. After stirring for 2 hours at room temperature, the reaction mixture is hydrolysed with an aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic phase is washed with water and dried over anhydrous sodium sulphate and the solvents are evaporated under reduced pressure. The expected product is obtained by filtration of the crystallized evaporation residue taken up in n-pentane;

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customthe solvents are evaporated under reduced pressure

Sources & evidence

ORD record
ord-9c07f9b31b9f40aa99e4f90004a6c7ee
Source dataset
uspto-grants-2004_01
Patent number
US06673790B1

Reaction notes

Loading…