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

HRID 1918076Notes

Reaction equation

HRID 1918076 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-57a2a57061574e008b1bb2132d44e5c1
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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