Imidazole → N-[3-acetylamino-2-(tert-butyldimethylsilanyloxy) propyl]acetamide

HRID 76239노트

반응식

HRID 76239 반응식
[C:1]([NH:4][CH2:5][CH:6]([OH:12])[CH2:7][NH:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].N1C=CN=C1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19].O.CCOCC>CN(C=O)C>[C:9]([NH:8][CH2:7][CH:6]([O:12][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23])[CH2:5][NH:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 332254HCID 332254, 화합물HCID 21584184Diethylether water

생성물 1

HCID 86698889N-[3-acetylamino-2-(tert-butyldimethylsilanyloxy) propyl]acetamide수율 93%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of N-(3-acetylamino-2-hydroxypropyl)acetamide (synthesized as described in J. Org. Chem., 2000, 65(4), 1200, which is incorporated herein by reference in its entirety) (741 mg, 4.25 mmol) and 1H-imidazole (579 mg, 8.51 mmol) in dry DMF (17 mL), a solution of tert-butylchlorodimethylsilane (962 mg, 6.38 mmol) in dry DMF (8 mL) was added dropwise, and the reaction was stirred at r.t. overnight. The reaction was portioned between H2O/Et2O, the phases were separated and the aqueous layer was washed twice with Et2O and three times with EtOAc. All the organics were combined, dried over Na2SO4, filtered and concentrated, affording N-[3-acetylamino-2-(tert-butyldimethylsilanyloxy) propyl]acetamide (1140 mg, 3.95 mmol, 93% yield) as off-white solid.

후처리

  1. customthe phases were separated
  2. washthe aqueous layer was washed twice with Et2O and three times with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-517a872a26be4324b062ae8078ef9fc6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835494B2

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