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

HRID 1008306ノート

反応式

HRID 1008306 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
115 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f12e47340f0645669d38950fdef6a5d4
出典データセット
uspto-grants-2004_09
特許番号
US06797723B1

反応ノート

読み込み中…