Potassium Carbonate → HCID 178501796, compound

HRID 1526513Notes

Reaction equation

HRID 1526513 reaction equation
[CH2:1]([C:8]([OH:18])([C:14]([NH:16][NH2:17])=O)[C:9]([O:11][CH2:12]C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([O:29][CH3:30])[CH:28]=1)[C:24]#[N:25].C([O-])([O-])=O.[K+].[K+].[Si](C=[N+]=[N-])(C)(C)C>C(O)CCC.C(OCC)(=O)C.O.CO>[CH3:30][O:29][C:27]1[CH:26]=[C:23]([C:24]2[NH:25][C:14]([C:8]([OH:18])([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:9]([O:11][CH3:12])=[O:10])=[N:16][N:17]=2)[CH:22]=[C:21]([O:20][CH3:19])[CH:28]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 294821-(Cyanomethyl)-3,5-dimethoxybenzeneHCID 167693TrimethylsilyldiazomethaneHCID 89500260Ethyl 2-benzyl-3-hydrazinyl-2-hydroxy-3-oxopropanoate

Product 1

HCID 178501796HCID 178501796, compound

Reagents, catalysts & solvents 4

HCID 2631-ButanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

To the mixture of ethyl 2-benzyl-3-hydrazinyl-2-hydroxy-3-oxopropanoate (40 mg), 3,5-dimethoxybenzonitrile (55 mg) and K2CO3 (44 mg) in 2 mL of n-butanol was heated at 160° C. for 1.5 h. The mixture was then diluted with ethyl acetate and water. The aqueous layer was washed with ethyl acetate and then acidified until pH=1. The mixture was then extracted with 30% isopropanol in chloroform. The organic layer was dried with magnesium sulfate and concentrated to give the crude acid, which was then dissolved in methanol. To the resulting solution was added TMSCHN2 (0.3 mL, 2 M in Et2O) at rt. After 30 min, the mixture was concentrated and purified by Gilson RP-HPLC (30-100% ACN/water/0.05% TFA) to give methyl 2-[5-(3,5-dimethoxyphenyl)-4H-1,2,4-triazol-3-yl]-2-hydroxy-3-phenylpropanoate as a yellow oil.

Workup

  1. washThe aqueous layer was washed with ethyl acetate
  2. extractionThe mixture was then extracted with 30% isopropanol in chloroform
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. concentrationconcentrated
  5. customto give the crude acid, which
  6. concentrationthe mixture was concentrated
  7. custompurified by Gilson RP-HPLC (30-100% ACN/water/0.05% TFA)

Sources & evidence

ORD record
ord-e2368da196e24b17b7d4a09c41c97ad3
Source dataset
uspto-grants-2015_07
Patent number
US09085568B2

Reaction notes

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