Methyl 4-methoxyacetoacetate → HCID 178496271, 화합물

HRID 1624644노트

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HRID 1624644 반응식
[F:1][C:2]1([F:16])[O:7][C:6]2[CH:8]=[C:9]([F:13])[C:10]([NH2:12])=[CH:11][C:5]=2[O:4][C:3]1([F:15])[F:14].[N:17]([O-])=O.[Na+].[CH3:21][O:22][CH2:23][C:24](=[O:30])[CH2:25][C:26]([O:28][CH3:29])=[O:27].CC([O-])=O.[Na+]>Cl.O.CCO>[CH3:21][O:22][CH2:23][C:24](=[O:30])[C:25](=[N:17][NH:12][C:10]1[C:9]([F:13])=[CH:8][C:6]2[O:7][C:2]([F:1])([F:16])[C:3]([F:15])([F:14])[O:4][C:5]=2[CH:11]=1)[C:26]([O:28][CH3:29])=[O:27]

참가 물질

8

반응물 4

HCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 144057012,2,3,3,7-Pentafluoro-2,3-dihydro-1,4-benzodioxin-6-amineHCID 23668193Sodium Nitrite

생성물 1

HCID 178496271HCID 178496271, 화합물수율 85%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매HCID 962Water용매

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온도
0 °C

실험 절차

To a suspension of 2,2,3,3,7-pentafluoro-2,3-dihydro-1,4-benzodioxin-6-amine (4.87 g, 20.2 mmol) in 6 M HCl aqueous solution (20.2 mL) was added a solution of NaNO2 (1.67 g, 24.2 mmol) in water (4 mL) at 0° C. The mixture was stirred at 0° C. for 15 min. To a suspension of methyl 4-methoxy-3-oxobutanoate (2.61 mL, 20.2 mmol) and NaOAc (303 g) in EtOH (34 mL) was added the above solution at 0° C. The mixture was stirred at 0° C. for 15 min. The precipitates were collected by filtration, washed with water, dissolved in EtOAc, washed with brine, dried over MgSO4, filtered and concentrated in vacuo to yield the title compound (6.84 g, 85% yield) as a red solid: 1H NMR (DMSO-d6, 300 MHz): 8 ppm 3.33 (3H, s), 3.82 (3H, s), 4.68 (2H, s), 7.66-7.93 (2H, m), 12.16 (1H, brs).

후처리

  1. additionwas added the above solution at 0° C
  2. stirringThe mixture was stirred at 0° C. for 15 min
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. dissolutiondissolved in EtOAc
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f4e9726c7f8e4389b467a9058afe9c11
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778944B2

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