2-Hydroxyisobutyric acid → 2-methyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanol

HRID 1014329노트

반응식

HRID 1014329 반응식
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[NH:9][CH2:8][CH2:7]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:40][C:41]([CH3:46])([CH3:45])[C:42](O)=[O:43].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:45][C:41]([OH:40])([CH3:46])[C:42]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([O:3][CH3:2])=[C:12]([N+:13]([O-:15])=[O:14])[CH:11]=2)[CH2:7][CH2:8]1)=[O:43]

참가 물질

6

반응물 4

HCID 116712-Hydroxyisobutyric acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673167385-(methyloxy)-6-nitro-2,3-dihydro-1H-indole hydrochloride

생성물 1

HCID 594421262-methyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanol수율 69.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole hydrochloride (1 g, 4.34 mmol) in DMF (50 mL) was added HATU (9.89 g, 26.0 mmol), 2-hydroxy-2-methylpropanoic acid (0.677 g, 6.50 mmol), and DIPEA (2.272 mL, 13.01 mmol). After stirring overnight at rt, the solvent was removed, the residue was redissolved in DCM (100 mL), washed with 1M HCl (100 mL), adsorbed to silica gel, and purified by column chromatography (10% to 40% ethyl acetate/hexanes) to afford 2-methyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanol (0.84 g, 69%). ESIMS (M+H)+=281.

후처리

  1. customthe solvent was removed
  2. dissolutionthe residue was redissolved in DCM (100 mL)
  3. washwashed with 1M HCl (100 mL)
  4. custompurified by column chromatography (10% to 40% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-38d3fdc5f32448689d578ca0bfb4894f
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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