Acetic Acid → HCID 18753000, compound

HRID 1838223Notes

Reaction equation

HRID 1838223 reaction equation
C(O)(=O)C.C(O[C:8]1(O[Si](C)(C)C)[CH2:10][CH2:9]1)C.[NH2:16][C:17]1[CH:42]=[CH:41][C:20]([CH2:21][N:22]2[C:30]3[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=3)[C:24]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:39])([CH3:32])[C:23]2=[O:40])=[C:19]([O:43][CH3:44])[CH:18]=1.C([BH3-])#N.[Na+]>CO>[Cl:31][C:27]1[CH:26]=[C:25]2[C:30](=[CH:29][CH:28]=1)[N:22]([CH2:21][C:20]1[CH:41]=[CH:42][C:17]([NH:16][CH:8]3[CH2:10][CH2:9]3)=[CH:18][C:19]=1[O:43][CH3:44])[C:23](=[O:40])[C:24]2([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[Cl:39])[CH3:32]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 15521770HCID 15521770, compound

Product 1

HCID 18753000HCID 18753000, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.54 ml of acetic acid, 0.4 g of 3 Å molecular sieve and 0.207 ml of (1-ethoxycyclopropyl)oxytrimethylsilane are added to 0.4 g of the compound of Example 48 in solution in 10 ml of methanol. After stirring for 30 minutes at room temperature, 0.265 g of sodium cyanoborohydride is added and then the mixture is heated at reflux for 10 hours. After cooling, hydrolysis is carried out with 20 ml of 2N sodium hydroxide solution, filtration is carried out through celite and the celite is rinsed with ethyl acetate. The organic phase is washed with a 10% aqueous sodium chloride solution and dried over sodium sulphate and the solvents are evaporated under reduced pressure.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 10 hours
  3. temperatureAfter cooling
  4. customhydrolysis
  5. filtrationis carried out with 20 ml of 2N sodium hydroxide solution, filtration
  6. washthe celite is rinsed with ethyl acetate
  7. washThe organic phase is washed with a 10% aqueous sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. customthe solvents are evaporated under reduced pressure

Sources & evidence

ORD record
ord-556ffacc27434c2898af4b00026f4f0f
Source dataset
uspto-grants-2004_01
Patent number
US06673790B1

Reaction notes

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