Ammonium Chloride → HCID 66960914, compound

HRID 1446508Notes

Reaction equation

HRID 1446508 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9](=[O:32])[CH:10]([NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])P(OOCC)(OOCC)=O.[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][C:42]=1[N:43]1[CH:47]=[C:46]([CH3:48])[N:45]=[CH:44]1)[CH:38]=O.[Cl-].[NH4+]>C(OCC)(=O)C.C(Cl)Cl>[CH3:7][O:8][C:9](=[O:32])/[C:10](/[NH:21][C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])=[CH:38]/[C:37]1[CH:40]=[CH:41][C:42]([N:43]2[CH:47]=[C:46]([CH3:48])[N:45]=[CH:44]2)=[C:35]([O:34][CH3:33])[CH:36]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86602478HCID 86602478, compound

Product 1

HCID 66960914HCID 66960914, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

To a methylene chloride (10 mL) suspension of potassium tert-butoxide (290 mg), a methylene chloride (3 mL) solution of benzyloxycarbonylamino(diethoxyphosphono)acetic acid methyl ester (850 mg) was added dropwise at −70° C. After agitating the reaction solution at −70° C. for 2 hours, a methylene chloride (7 mL) solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (500 mg) obtained in Example 1 was added dropwise. The reaction solution was agitated at −70° C. for 1 hour, and then agitated at room temperature for 4 hours. Ethyl acetate and a saturated ammonium chloride solution were added to the reaction solution after the reaction ended, and the organic layer was separated. After drying the obtained organic layer with anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate 4:1→elution solvent:hexane:ethyl acetate), and 433 mg (45%) of (Z)-2-benzyloxycarbonylamino-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid methyl ester was obtained. The physical properties of the compound are as follows.

Workup

  1. stirringThe reaction solution was agitated at −70° C. for 1 hour
  2. stirringagitated at room temperature for 4 hours
  3. customthe organic layer was separated
  4. dry with materialAfter drying the obtained organic layer with anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate 4:1→elution solvent:hexane:ethyl acetate)

Sources & evidence

ORD record
ord-dfd37be5900646eeb1adf678da08bb74
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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