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

HRID 1170606

반응식

HRID 1170606 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-e728478c0c6f41978e94f4b7a22af884
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825238B2

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