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1,4-Dioxane → 2-(3-Aminoisoxazol-5-yl)-2-methylpropyl 4-nitrobenzenesulfonate

HRID 871675
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인쇄 미리보기

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HRID 871675 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([O:13][CH2:14][C:15]([CH3:32])([C:17]2[O:21][N:20]=[C:19]([NH:22]C(OC3C=CC=CC=3)=O)[CH:18]=2)[CH3:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[O-2].[Mg+2].O1CCOCC1>O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([O:13][CH2:14][C:15]([C:17]2[O:21][N:20]=[C:19]([NH2:22])[CH:18]=2)([CH3:16])[CH3:32])(=[O:11])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]
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참가 물질

5

반응물 3

HCID 312751,4-DioxaneHCID 6850729Magnesium monoxideHCID 866535272-Methyl-2-(3-(phenoxycarbonylamino)isoxazol-5-yl)propyl 4-nitrobenzenesulfonate

생성물 1

HCID 866535282-(3-Aminoisoxazol-5-yl)-2-methylpropyl 4-nitrobenzenesulfonate수율 87.9%

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

A stirred mixture of 2-methyl-2-(3-(phenoxycarbonylamino)isoxazol-5-yl)propyl 4-nitrobenzenesulfonate (130 mg, 0.22 mmol), magnesium oxide (45 mg, 0.87 mmol), 1,4-dioxane (8 mL) and water (2 mL) was stirred at 60° C. for 5 h. The reaction mixture was cooled to rt and filtrated. The filtrate was concentrated under reduced pressure to give the crude product. Purification via recrystallization from a 1:1 mixture of diethyl ether and hexane, afforded 2-(3-aminoisoxazol-5-yl)-2-methylpropyl 4-nitrobenzenesulfonate (66 mg, 69%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.38-8.40 (m, 2H), 7.99-8.00 (m, 2H), 5.55 (s, 1H), 4.13 (s, 2H), 1.32 (s, 6H).

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltrated
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give the crude product
  5. customPurification
  6. customvia recrystallization
  7. additionfrom a 1:1 mixture of diethyl ether and hexane

출처 및 근거

ORD 기록
ord-c68b4d3c347c4f419f1f828f98fc589a
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08969587B2

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