Hydroxyamine hydrochloride → HCID 178436628, 화합물

HRID 245088노트

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HRID 245088 반응식
[CH3:1][C:2]1([CH3:20])[O:6][C@H:5]([CH2:7][O:8][C:9]2[C:16]([CH3:17])=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[CH2:18][CH3:19])[CH2:4][O:3]1.C([O-])(O)=O.[Na+].Cl.[NH2:27][OH:28]>CO>[CH3:1][C:2]1([CH3:20])[O:6][C@H:5]([CH2:7][O:8][C:9]2[C:16]([CH3:17])=[CH:15][C:12]([C:13]([NH:27][OH:28])=[NH:14])=[CH:11][C:10]=2[CH2:18][CH3:19])[CH2:4][O:3]1

참가 물질

5

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HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 67491300(R)-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-ethyl-5-methyl-benzonitrile

생성물 1

HCID 178436628HCID 178436628, 화합물수율 107.7%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
60 °C

실험 절차

To a mixture of (R)-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-ethyl-5-methyl-benzonitrile (4.45 g, 16.2 mmol) and NaHCO3 (4.75 g, 56.6 mmol) in methanol (30 mL), hydroxylamine hydrochloride (3.37 g, 48.5 mmol) is added. The mixture is stirred at 60° C. for 18 h before it is filtered and the solvent of the filtrate is removed in vacuo. The residue is dissolved in EA and washed with a small amount of water and brine. The org. phase is separated, dried over MgSO4, filtered, concentrated and dried to give the title compound (5.38 g) as a white solid; LC-MS**: tR=0.46 min, [M+1]+=309.23; 1H NMR (D6-DMSO): δ 1.17 (t, J=7.5 Hz, 3H), 1.33 (s, 3H), 1.38 (s, 3H), 2.25 (s, 3H), 2.57-2.69 (m, 2H), 3.73-3.84 (m, 3H), 4.12 (t, J=7.0 Hz, 1H), 4.39-4.45 (m, 1H), 5.76 (s br, 2H), 7.34 (s, 1H), 7.36 (s, 1H), 9.47 (s, 1H).

후처리

  1. additionis added
  2. filtrationis filtered
  3. customthe solvent of the filtrate is removed in vacuo
  4. dissolutionThe residue is dissolved in EA
  5. washwashed with a small amount of water and brine
  6. customphase is separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customdried

출처 및 근거

ORD 기록
ord-787fe59449ef4637bc61e4fcfd0aeef5
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658675B2

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