Hydroxyamine hydrochloride → HCID 178426650, 화합물

HRID 1820951노트

반응식

HRID 1820951 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 178426650HCID 178426650, 화합물수율 58.1%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6fa6cca7acb049bfa10d5b26f69e060e
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605171B2

반응 노트

불러오는 중…