Hydrochloric Acid → Ethyl 3-hydroxy-3-(1-trityl-1h-imidazol-4-yl)propanoate

HRID 2044817Notes

Reaction equation

HRID 2044817 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH:25]=[O:26])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:28]([O:31][CH2:32][CH3:33])(=[O:30])[CH3:29]>CC1CCCO1.C1COCC1>[OH:26][CH:25]([C:23]1[N:22]=[CH:21][N:20]([C:1]([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:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:24]=1)[CH2:29][C:28]([O:31][CH2:32][CH3:33])=[O:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehyde

Product 1

HCID 21879633Ethyl 3-hydroxy-3-(1-trityl-1h-imidazol-4-yl)propanoateYield 83%

Reagents, catalysts & solvents 2

HCID 73012-MethyltetrahydrofuranSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under argon atmosphere, 8.3 mL (4.43 mmol, 1.5 equivalent) of the solution of ethyl bromozincacetate in 2-methyltetrahydrofuran obtained in Example 67 was added dropwise to a solution of 1 g (2.96 mmol) of 1-trityl-1H-imidazol-4-carbaldehyde in 10 mL of THF at 5˜8° C. The mixture was stirred at 3˜6° C. for 2 hours and 20 minutes. The mixture was stirred at 20˜25° C. for 1 hour and 15 minutes. 10 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 (×2) of 1N hydrochloric acid, 5 mL of water, 5 mL (×2) of an aqueous saturated sodium bicarbonate solution, and 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 5 mL of IPE afforded 1.04 g of the desired product (yield 83%).

Workup

  1. stirringThe mixture was stirred at 20˜25° C. for 1 hour and 15 minutes
  2. customThen, the layers were separated
  3. washThe organic layer was washed successively with 5 mL (×2) of 1N hydrochloric acid, 5 mL of water, 5 mL (×2) of an aqueous saturated sodium bicarbonate solution, and 5 mL (×2) of an aqueous saturated sodium chloride solution
  4. washAfter washing
  5. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  6. concentrationAfter concentration
  7. customunder reduced pressure, recrystallization with 5 mL of IPE

Sources & evidence

ORD record
ord-10bbc0e4390546e29f43c86549c72d0c
Source dataset
uspto-grants-2013_11
Patent number
US08586762B2

Reaction notes

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