Hydroxyamine hydrochloride → HCID 178426650、化合物

HRID 1820951ノート

反応式

HRID 1820951 の反応式
C[C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].Cl.[NH2:20][OH:21].[C:22](=O)(O)[O-].[Na+]>CO>[OH:21][NH:20][C:8](=[NH:9])[C:7]1[CH:2]=[CH:3][C:4]([CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[C:5]([CH3:22])[CH:6]=1

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 68649344Tert-butyl 3-(4-cyano-3-methylphenyl)propanoate

生成物 1

HCID 178426650HCID 178426650、化合物収率 58.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2.5 g (10.2 mmol) of tert-butyl 3-(3-methyl-4-cyanophenyl) propionate (from Step B), 0.85 g (12.2 mmol) of hydroxylamine hydrochloride and 2.57 g (30.6 mmol) of sodium bicarbonate in 30 mL of methanol was heated in a sealed tube at 100° C. for 16 h. The reaction mixture was cooled to rt, then concentrated. The residue was partitioned between EtOAc (50 mL) and water (50 mL). The organic layer was separated and washed with sat'd NaCl (3×50 mL), dried over MgSO4, and concentrated. Chromatography on a Biotage 40M cartridge using 7:3 v/v hexanes/EtOAc as the eluant afforded 1.65 g (58%) of the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.45 (s, 9H), 2.40 (s, 3H), 2.54 (t, J=7.8, 2H), 2.90 (t, J=7.8, 2H), 5.05 (s, 2H), 7.04 (d, J=7.8, 1H), 7.08 (s, 1H), 7.27 (d, J=7.8, 1H).

後処理

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated
  3. customThe residue was partitioned between EtOAc (50 mL) and water (50 mL)
  4. customThe organic layer was separated
  5. washwashed with sat'd NaCl (3×50 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-6fa6cca7acb049bfa10d5b26f69e060e
出典データセット
uspto-grants-2009_10
特許番号
US07605171B2

反応ノート

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