Hydrochloric Acid → HCID 22847667, compound

HRID 6485Notes

Reaction equation

HRID 6485 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH:5][CH2:6][C:7]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:10]([CH2:20][CH2:21][CH2:22][CH3:23])=[N:9][CH:8]=1.[CH2:32]=O.Cl>C(O)=O>[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[N:5]([CH2:6][C:7]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:10]([CH2:20][CH2:21][CH2:22][CH3:23])=[N:9][CH:8]=1)[CH3:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 54447244HCID 54447244, compound

Product 1

HCID 22847667HCID 22847667, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

N-[{1-[(2-Chlorophenyl)methyl]-2-n-butyl-1H-imidazol-5-yl}methyl]phenylalanine methyl ester (prepared in Example 3(i) method B) (o.52 g, 1.18 mmol), 88% formic acid (0.31 g), and 37% aqueous formaldehyde (o.44 g) were heated over a steam bath for 18 hours. The reaction mixture was poured into 10% hydrochloric acid solution and then extracted with diethyl ether. The aqueous layer was basified to pH 10 with 10% sodium hydroxide solution and then the product was extracted into ethyl acetate. The organic extract was dried with anhydrous magnesium sulfate and the solvent was removed in vacuo. The crude product was chromatographed on silica gel with 50% ethyl acetate in hexane to give 0.377 g (70%) of N-[{1-[(2-chlorophenyl)methyl]-2-n-butyl-1H-imidazol -5-yl}methyl]-N-methylphenylalanine methyl ester. Hydrolysis of the ester following the procedure of Example 2(ii) gave the title compound as a foam (0.265 g, 77%); mp 59°-61° C.

Workup

  1. extractionextracted with diethyl ether
  2. extractionthe product was extracted into ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried with anhydrous magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customThe crude product was chromatographed on silica gel with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-88e25dc0a82b4570b0c9e6e0b265c717
Source dataset
uspto-grants-1993_09
Patent number
US05248689

Reaction notes

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