Hydrochloric Acid → ethyl 3-hydroxy-3-(5-methyl-1-trityl-1H-imidazol-4-yl)propanoate

HRID 2044808Notes

Reaction equation

HRID 2044808 reaction equation
[CH3:1][C:2]1[N:6]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[N:4][C:3]=1[CH:26]=[O:27].Cl.[C:29]([O:32][CH2:33][CH3:34])(=[O:31])[CH3:30]>O1CCCC1>[OH:27][CH:26]([C:3]1[N:4]=[CH:5][N:6]([C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:2]=1[CH3:1])[CH2:30][C:29]([O:32][CH2:33][CH3:34])=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 118243385-methyl-1-trityl-1H-imidazole-4-carbaldehyde

Product 1

HCID 23031687ethyl 3-hydroxy-3-(5-methyl-1-trityl-1H-imidazol-4-yl)propanoateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon atmosphere, 3.2 mL (1.70 mmol, 2 equivalents) of the solution of ethyl bromozincacetate in tetrahydrofuran obtained in Example 43 was added dropwise to a solution of 0.3 g (0.85 mmol) of 5-methyl-1-trityl-1H-imidazol-4-carbaldehyde in 3 mL of THF at 4˜7° C. The mixture was stirred at 2˜5° C. for 2 hours. 5 mL of 1N hydrochloric acid was added dropwise at 20° C. or lower, followed by dilution with 15 mL of ethyl acetate. Then, the layers were separated. The organic layer was washed successively with 5 mL of 1N hydrochloric acid, 5 mL of water, 2.5 mL (×2) of an aqueous saturated sodium bicarbonate solution, and 2.5 mL (×2) of an aqueous saturated sodium chloride solution. After washing, the organic layer was dried with anhydrous magnesium sulfate. After concentration under reduced pressure, recrystallization with 3 mL of IPE afforded 0.30 g of the desired product (yield 80%).

Workup

  1. customThen, the layers were separated
  2. washThe organic layer was washed successively with 5 mL of 1N hydrochloric acid, 5 mL of water, 2.5 mL (×2) of an aqueous saturated sodium bicarbonate solution, and 2.5 mL (×2) of an aqueous saturated sodium chloride solution
  3. washAfter washing
  4. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  5. concentrationAfter concentration
  6. customunder reduced pressure, recrystallization with 3 mL of IPE

Sources & evidence

ORD record
ord-100a318d68594acfb1e6464ac9d34196
Source dataset
uspto-grants-2013_11
Patent number
US08586762B2

Reaction notes

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