Dimethylformamide → 2-(3-{3-[2-Ethyl-5-hydroxy-4-(2H-pyrazol-3-yl)phenoxy]propoxy}-2-propyl-phenoxy)benzoic acid

HRID 1008306Notes

Reaction equation

HRID 1008306 reaction equation
C[O:2][C:3](=[O:44])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([O:28]CC3C=CC=CC=3)[C:25]([C:36](=O)[CH3:37])=[CH:24][C:23]=2[CH2:39][CH3:40])[C:12]=1[CH2:41][CH2:42][CH3:43].COC(OC)[N:48](C)C.C[N:54]([CH3:57])C=O>C(OCC)(=O)C.Cl>[CH2:39]([C:23]1[CH:24]=[C:25]([C:36]2[NH:48][N:54]=[CH:57][CH:37]=2)[C:26]([OH:28])=[CH:27][C:22]=1[O:21][CH2:20][CH2:19][CH2:18][O:17][C:13]1[C:12]([CH2:41][CH2:42][CH3:43])=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:2])=[O:44])[CH3:40]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 601111702-{3-[3-(4-Acetyl-5-benzyloxy-2-ethylphenoxy)propoxy]-2-propyl-phenoxy}benzoic acid methyl ester

Product 1

HCID 1355289882-(3-{3-[2-Ethyl-5-hydroxy-4-(2H-pyrazol-3-yl)phenoxy]propoxy}-2-propyl-phenoxy)benzoic acidYield 63%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 2-(3-{3-[4-acetyl-5-benzyloxy-2-ethylphenoxy]propoxy}-2-propylphenoxy)benzoic acid methyl ester (3.07 g, 5.04 mmol) and dimethylformamide dimethylacetal (0.9 mL, 7 mmol) in N,N-dimethylformamide (3 mL) was heated at 110-120° C. for 35 h. The mixture was cooled to room temperature and diluted with a mixture of ethyl acetate and 1 N hydrochloric acid. The organic layer was separated, washed twice with water, once with saturated sodium chloride solution, dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 30% ethyl acetate/70% hexane to ethyl acetate) of the residue provided 2.1 g (63%) of the title compound as a yellow oil. TQF MS ES+ exact mass calculated for C40H46NO7 (p+1): m/z=652.3274. Found: 652.3270. IR (CHCl3, cm−1) 2965, 1720, 1605. Anal. Calcd for C40H45NO7: C, 73.71; H, 6.96; N, 2.15. Found: C, 73.72; H, 6.95; N, 2.18.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed twice with water, once with saturated sodium chloride solution
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f12e47340f0645669d38950fdef6a5d4
Source dataset
uspto-grants-2004_09
Patent number
US06797723B1

Reaction notes

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