Hydrochloric Acid → 4-(3-Fluoro-5-((4-(2-methyl-1H-imidazol-1-YL)benzyl)oxy)phenyl)tetrahydro-2H-pyran-4-carboxylic acid

HRID 1108071ノート

反応式

HRID 1108071 の反応式
[F:1][C:2]1[CH:3]=[C:4]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[CH:30][N:29]=[C:28]3[CH3:32])=[CH:23][CH:22]=2)[CH:5]=[C:6]([C:8]2([C:14]([O:16]CC)=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1.[OH-].[Li+].CO.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[CH:30][N:29]=[C:28]3[CH3:32])=[CH:23][CH:22]=2)[CH:5]=[C:6]([C:8]2([C:14]([OH:16])=[O:15])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 11339601HCID 11339601、化合物

生成物 1

HCID 113158374-(3-Fluoro-5-((4-(2-methyl-1H-imidazol-1-YL)benzyl)oxy)phenyl)tetrahydro-2H-pyran-4-carboxylic acid収率 96%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A stirred mixture of ethyl 4-[5-fluoro-3-[4-(2-methylimidazol-1-yl)benzyloxy]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate (Example 2) (1.10 g, 25 mmol), an aqueous solution of lithium hydroxide (0.13 g, 30 mmol, 5 ml), methanol (15 ml) and THF (15 ml) was refluxed for 24 hr. The reaction mixture was neutralized with 1N hydrogen chloride. Volatiles were removed by evaporation under reduced pressure. The residue was suspended into a mixture of water (20 ml) and phosphate buffer (pH=7, 5 ml) and heated to reflux for 30 min. After cooling to 0° C., solids were collected by filtration, washed with water and then with ether and dried to constant weight under vacuum at 80° C. for 14 hr to afford the titled compound as white solids (0.98 g, 96%).

後処理

  1. customVolatiles were removed by evaporation under reduced pressure
  2. additionThe residue was suspended into a mixture of water (20 ml) and phosphate buffer (pH=7, 5 ml)
  3. temperatureheated
  4. temperatureto reflux for 30 min
  5. filtrationsolids were collected by filtration
  6. washwashed with water
  7. dry with materialwith ether and dried to constant weight under vacuum at 80° C. for 14 hr

出典と根拠

ORDレコード
ord-26394ef2b08c4c44bdb9cc54e3fbfccc
出典データセット
uspto-grants-2000_05
特許番号
US06063928

反応ノート

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