Hydrochloric Acid → 2-Ethoxycarbonyl-2,2-difluoro-1-phenylethyl 1-adamantanecarboxylate

HRID 58517

反応式

HRID 58517 の反応式
[F:1][C:2]([F:16])([CH:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:17]12([C:27](Cl)=[O:28])[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2.C(N(CC)CC)C.Cl>C(Cl)Cl>[CH2:6]([O:5][C:3]([C:2]([F:16])([F:1])[CH:8]([O:15][C:27]([C:17]12[CH2:26][CH:21]3[CH2:20][CH:19]([CH2:25][CH:23]([CH2:22]3)[CH2:24]1)[CH2:18]2)=[O:28])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:4])[CH3:7]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 11138943Ethyl 2,2-difluoro-3-hydroxy-3-phenylpropanoate

生成物 1

HCID 1179666922-Ethoxycarbonyl-2,2-difluoro-1-phenylethyl 1-adamantanecarboxylate収率 97.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Ethyl 2,2-difluoro-3-hydroxy-3-phenylpropionate acid (9 g) prepared in Synthesis Example 1-4 and 1-adamantanecarbonyl chloride (9.5 g) were dissolved in methylene chloride (60 g), and a mixed solution of triethyl amine (6 g), 4-dimethyl aminopyridine (0.5 g) and methylene chloride (20 g) was dropped into the obtained solution under ice cooling. After aging overnight, 5% by mass hydrochloric acid was added to the product and quenched, and then the reaction solution was washed with water, and concentrated. Methylisobutyl ketone was added to the concentrated solution, and was concentrated again to obtain a target compound, or 1-adamantane carboxylic acid 2-ethoxycarbonyl-2,2-difluoro-1-phenyl-ethyl ester (15 g) as a colorless oily matter (yield: 68%).

後処理

  1. customquenched
  2. washthe reaction solution was washed with water
  3. concentrationconcentrated
  4. additionMethylisobutyl ketone was added to the concentrated solution
  5. concentrationwas concentrated again

出典と根拠

ORDレコード
ord-b559aa3f57f942a1bb5d1fd0236eb0b3
出典データセット
uspto-grants-2016_09
特許番号
US09436083B2

関連ノート

読み込み中…