Imidazole → t-Butyldimethylsilyloxyserine methyl ester

HRID 1734684노트

반응식

HRID 1734684 반응식
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].CN(C=[O:27])C>CCOCC>[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH:6][O:27][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

생성물 1

HCID 22856314t-Butyldimethylsilyloxyserine methyl ester

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
25 °C

실험 절차

Serine methyl ester hydrochloride [HOCH2CH(NH2)CO2CH3. HCl] (18.7 g; 0.120 mol) and imidazole (30 g; 0.44 mol) are dissolved in DMF (100 ml) and cooled to 0° C. t-Butyldimethylsilyl chloride (19.5 g; 0.13 mol) is added and the reaction allowed to stir 15 hours at 25° C. The reaction is then diluted with ether (2 L), washed with water (4x 500 ml), dried (MgSO4) and concentrated to yield t-butyldimethylsilyloxyserine methyl ester as an oil which is used directly in Step B.

후처리

  1. additionis added
  2. washwashed with water (4x 500 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e6de6bce13894bee8a8e60dfb2cbcae9
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05534532

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