Acetone → HCID 68877555, compound

HRID 1787840Notes

Reaction equation

HRID 1787840 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([C:19](=[O:25])[CH:20](OCC)O)=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[N:38]=[C:37]([CH3:39])[N:36]([CH2:40][CH2:41][C:42]([NH2:45])([CH3:44])[CH3:43])[N:35]=2)=[CH:30][CH:29]=1.[BH4-].[Na+].CC(C)=O>C(O)C.C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH:19]([OH:25])[CH2:20][NH:45][C:42]([CH3:44])([CH3:43])[CH2:41][CH2:40][N:36]2[C:37]([CH3:39])=[N:38][C:34]([C:31]3[CH:30]=[CH:29][C:28]([O:27][CH3:26])=[CH:33][CH:32]=3)=[N:35]2)=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 59754203HCID 59754203, compoundHCID 68858509Methyl benzyloxy-5-(2-ethoxy-2-hydroxy-acetyl)-benzoate

Product 1

HCID 68877555HCID 68877555, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

8.5 g of methyl 2-benzyloxy-5-(2-ethoxy-2-hydroxy-acetyl)-benzoate and 4.9 g of 3-[3-(4-methoxy-phenyl)-5-methyl-[1,2,4]triazol-1-yl]-1,1-dimethyl-propylamine in 100 mL ethanol are stirred for three hours at 60° C., cooled to 10° C., combined batchwise with 0.8 g of sodium borohydride and stirred for a further three hours at ambient temperature. Then 10 mL acetone are added and the mixture is stirred for one hour. It is then poured onto ice and acidified with glacial acetic acid. The ethanol is distilled off, the aqueous phase remaining is made alkaline with sodium hydroxide and extracted with ethyl acetate. The organic phases are dried with sodium sulphate and evaporated down. The residue is combined with 80 mL ethanol, acidified with 3.2 g of oxalic acid, dissolved in ethanol, and seeded. The product that crystallises out is suction filtered and washed. Yield: 8 g (69%, oxalate); m.p.=210-213° C.

Workup

  1. stirringthe mixture is stirred for one hour
  2. additionIt is then poured onto ice
  3. distillationThe ethanol is distilled off
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phases are dried with sodium sulphate
  6. customevaporated down
  7. dissolutiondissolved in ethanol
  8. customThe product that crystallises out is suction
  9. filtrationfiltered
  10. washwashed

Sources & evidence

ORD record
ord-9f34e6e3d751450c9ab46d4ded2de53c
Source dataset
uspto-grants-2009_03
Patent number
US07511067B2

Reaction notes

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