Hydrochloric Acid → 4-Benzyloxycarbonylamino-4-difluoromethylbutyric acid

HRID 2286118ノート

反応式

HRID 2286118 の反応式
[NH2:1][CH:2]([CH:8]([F:10])[F:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].Cl[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].Cl>[OH-].[Na+].O1CCOCC1>[CH2:15]([O:14][C:12]([NH:1][CH:2]([CH:8]([F:10])[F:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 13050369HCID 13050369、化合物

生成物 1

HCID 205433414-Benzyloxycarbonylamino-4-difluoromethylbutyric acid

試薬・触媒・溶媒 2

HCID 14798Sodium Hydroxide溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 2 mmole of 4-amino-4-difluoromethylbutyric acid in 5 ml of 1 N sodium hydroxide at 0° C. are added simultaneously from two syringes 2 mmole of benzyl chloroformate in 1 ml of dioxane and 2 ml of 1 N sodium hydroxide. After 30 minutes at 0° C. the solution is acidified by the addition of 6 N hydrochloric acid, then extracted well with dichloromethane. The organic phase is dried and concentrated to afford 4-benzyloxycarbonylamino-4-difluoromethylbutyric acid which is dissolved in 15 ml of dichloromethane and treated with 2 mmole of thionyl chloride at 25° C. for 1 hour after which 4 mmole of propyl amine is added. The solution is stirred at 25° C. for one hour, then washed with water, dried and concentrated. The residue is treated with 6 ml of a solution of dioxane containing 40% w/w hydrogen bromide and allowed to stand for 30 minutes at 25° C. after which 50 ml of ether is added. The resulting precipitate is collected to afford N-propyl 4-amino-4-difluoromethylbutyramide hydrobromide.

後処理

  1. extractionextracted well with dichloromethane
  2. customThe organic phase is dried
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-52b367a7d79041719f64bcae7b2e4db4
出典データセット
uspto-grants-1982_04
特許番号
US04326071

反応ノート

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