Chloroiodomethane → 2,2-Dimethyl-3-(N-CBz-D-valyloxy)-propionic acid chloromethyl ester

HRID 489019ノート

反応式

HRID 489019 の反応式
[CH3:1][C:2]([CH3:25])([CH2:6][O:7][C:8](=[O:24])[C@@H:9]([CH:21]([CH3:23])[CH3:22])[NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:3]([OH:5])=[O:4].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:44][CH2:45]I>O1CCOCC1>[Cl:44][CH2:45][O:4][C:3](=[O:5])[C:2]([CH3:1])([CH3:25])[CH2:6][O:7][C:8](=[O:24])[C@@H:9]([CH:21]([CH3:22])[CH3:23])[NH:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12]

参加物

5

反応物 3

HCID 11644ChloroiodomethaneHCID 2723671Tetrabutylammonium HydroxideHCID 233874902,2-dimethyl-3-(N-CBz-D-valyloxy)-propionic acid

生成物 1

HCID 537919342,2-Dimethyl-3-(N-CBz-D-valyloxy)-propionic acid chloromethyl ester

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

(2,2-dimethyl-3-(N-CBz-D-valyloxy)-propionic acid (4.5 g, 12.8 mmole) was dissolved in dioxane (20 ml). To the solution was added tetrabutylammonium hydroxide aqueous solution (40%, 8.3 ml, 12.8 mmole). The solution was dried in vacuo, and it was coevaporated with toluene several times. The residue was dissolved in methylene chloride and then chloroiodomethane (18 ml, 260 mmole) was added to the solution. After 18 hr, the reaction solution was evaporated and the product was isolated with silica gel column chromatography. 3.5 g.

後処理

  1. customThe solution was dried in vacuo, and it
  2. dissolutionThe residue was dissolved in methylene chloride
  3. customthe reaction solution was evaporated
  4. customthe product was isolated with silica gel column chromatography

出典と根拠

ORDレコード
ord-7c2427aa198541f89fd0852a49c94a9a
出典データセット
uspto-grants-2005_12
特許番号
US06974802B2

反応ノート

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