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

HRID 1014329ノート

反応式

HRID 1014329 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-38d3fdc5f32448689d578ca0bfb4894f
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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