Acetyl chloride → Methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate

HRID 927925노트

반응식

HRID 927925 반응식
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[C:15]([C:16]2[CH:20]=[CH:19][O:18][C:17]=2[CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:14][CH:13]=[C:12]([NH:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]>C(Cl)Cl.N1C=CC=CC=1>[C:1]([NH:5][C:6]1[C:15]([C:16]2[CH:20]=[CH:19][O:18][C:17]=2[CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:14][CH:13]=[C:12]([NH:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C:7]=1[C:8]([O:10][CH3:11])=[O:9])(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 6367Acetyl chlorideHCID 90071896Methyl 2-amino-3-[2-(tert-butyldimethylsilanyloxymethyl)furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate2회

생성물 1

HCID 90071968Methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

실험 절차

Acetyl chloride (0.09 mL) was added to a stirred solution of methyl 2-amino-3-[2-(tert-butyldimethylsilanyloxymethyl)furan-3-yl]-6-(2,2-dimethylpropionylamino)-benzoate (Intermediate 35, 0.47 g) in DCM (5 mL) and pyridine (0.16 mL) and the mixture was stirred at room temperature for 1 hour. The mixture was diluted with DCM and washed with water and brine, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 20-50% to give methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate (0.442 g) as a colourless foam.

후처리

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 20-50%

출처 및 근거

ORD 기록
ord-e6897daee7684f769bb187314220ea53
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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