Acetone → HCID 68877754, compound

HRID 1787838Notes

Reaction equation

HRID 1787838 reaction equation
[Cl-].[Ca+2].[Cl-].[CH2:4]([O:11][C:12]1[CH:21]=[CH:20][C:19]([C:22](=[O:35])[CH2:23][NH:24][C:25]([CH3:34])([CH3:33])[CH2:26][CH2:27][N:28]2[CH:32]=[N:31][N:30]=[CH:29]2)=[CH:18][C:13]=1[C:14](OC)=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[BH4-].[Na+].CC(C)=O>C(O)C.O1CCCC1.C(O)(=O)C>[CH2:4]([O:11][C:12]1[CH:21]=[CH:20][C:19]([CH:22]([OH:35])[CH2:23][NH:24][C:25]([CH3:34])([CH3:33])[CH2:26][CH2:27][N:28]2[CH:29]=[N:30][N:31]=[CH:32]2)=[CH:18][C:13]=1[CH2:14][OH:15])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 68877944HCID 68877944, compound

Product 1

HCID 68877754HCID 68877754, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

5 g of calcium chloride are dissolved in 50 mL ethanol. Then 10 g of methyl 2-benzyloxy-5-[2-(1,1-dimethyl-3-[1,2,4]triazol-4-yl-propylamino)-acetyl]-benzoate in 100 mL tetrahydrofuran are added and the mixture is cooled to 5° C. It is combined batchwise with 3.5 g of sodium borohydride and stirred overnight while heating to ambient temperature. 15 mL acetone are added to the reaction mixture and it is stirred for 30 minutes. Glacial acetic acid is added, the solvents are distilled off, 100 mL water are added to the residue and it is adjusted to pH 2 with conc. hydrochloric acid. It is washed once with ethyl acetate, then made basic with ammonia, diluted with 100 mL water and extracted twice with in each case 200 mL ethyl acetate. After the organic phase has been dried it is evaporated down and the residue is dissolved in acetonitrile. The mixture is acidified with glacial acetic acid and seed crystals are added. The product precipitated is suction filtered and recrystallised from acetonitrile. Yield: 6.5 g (43%, acetate); m.p.=139-141° C.

Workup

  1. temperaturewhile heating to ambient temperature
  2. stirringis stirred for 30 minutes
  3. distillationthe solvents are distilled off
  4. addition100 mL water are added to the residue and it
  5. washIt is washed once with ethyl acetate
  6. additiondiluted with 100 mL water
  7. extractionextracted twice with in each case 200 mL ethyl acetate
  8. customAfter the organic phase has been dried it
  9. customis evaporated down
  10. dissolutionthe residue is dissolved in acetonitrile
  11. additionare added
  12. customThe product precipitated
  13. filtrationfiltered
  14. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-25c24f0e1d404431b21b22ec9c290112
Source dataset
uspto-grants-2009_03
Patent number
US07511067B2

Reaction notes

Loading…