Methanol → 2,2-dimethyl-3-(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-propionic acid

HRID 1691860ノート

反応式

HRID 1691860 の反応式
C[O:2][C:3](=[O:23])[C:4]([CH3:22])([CH3:21])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=2)[CH2:8][CH2:7]1.CO.[OH-].[Na+]>O1CCCC1>[CH3:21][C:4]([CH3:22])([CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=2)[CH2:10][CH2:11]1)[C:3]([OH:23])=[O:2]

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 667381462,2-dimethyl-3-(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-propionic acid methyl ester

生成物 1

HCID 667381622,2-dimethyl-3-(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-propionic acid収率 95.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2,2-Dimethyl-3-(5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-propionic acid methyl ester (199 mg, 0.62 mmol) from above was dissolved in tetrahydrofuran (2 mL). Then methanol (4 mL) and sodium hydroxide solution (1N, 2 mL) were added. The mixture was stirred and refluxed for 8 hrs. Solvents were evaporated and the residue was dissolved in hot methanol. The solution was cooled to room temperature and hydrochloric acid (1N, 2 mL) was added. The resulting mixture was cooled in an ice bath and the solid was filtered and washed with water. The solid was dried in air to give 2,2-dimethyl-3-(5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-propionic acid (181.5 mg). The NMR spectrum obtained on the sample is compatible with its structure. LC-MS calcd for C15H21N3O4 (m/e) 307.34, obsd 308.1 (M+H).

後処理

  1. temperaturerefluxed for 8 hrs
  2. customSolvents were evaporated
  3. dissolutionthe residue was dissolved in hot methanol
  4. additionhydrochloric acid (1N, 2 mL) was added
  5. temperatureThe resulting mixture was cooled in an ice bath
  6. filtrationthe solid was filtered
  7. washwashed with water
  8. customThe solid was dried in air

出典と根拠

ORDレコード
ord-6f314bd27dde4f659a290128b5a991fc
出典データセット
uspto-grants-2012_04
特許番号
US08153644B2

反応ノート

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