Water → tert-butyl ((1-((3-(2-amino-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

HRID 1051006노트

반응식

HRID 1051006 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:23][N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:40][C:41]([NH2:43])=[O:42].O>CN(C)C=O>[NH2:43][C:41](=[O:42])[CH2:40][O:22][C:18]1[CH:17]=[C:16]([S:13]([N:12]2[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[CH:9][C:10]([CH2:23][N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[CH:11]2)(=[O:14])=[O:15])[CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 90168587tert-butyl ((5-(2-fluorophenyl)-1-((3-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

생성물 1

HCID 90168683tert-butyl ((1-((3-(2-amino-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

tert-Butyl ((5-(2-fluorophenyl)-1-((3-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 1h (100 mg, 0.22 mmol) was dissolved in 10 mL of N,N-dimethylformamide, followed by addition of cesium carbonate (215 mg, 0.66 mmol) and 2-bromoacetamide (61 mg, 0.44 mmol), and then the reaction solution was stirred for 16 h. 50 mL of water was added, and the reaction solution was extracted with dichloromethane (50 mL×3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with elution system B to obtain the title product tert-butyl ((1-((3-(2-amino-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 2a (100 mg, a yellow oil) in 90% yield.

후처리

  1. extractionthe reaction solution was extracted with dichloromethane (50 mL×3)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography with elution system B

출처 및 근거

ORD 기록
ord-400fdbf8392244bcb6e10a38c54c2940
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388133B2

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