Potassium Carbonate → (S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropane

HRID 25237

Reaction equation

HRID 25237 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[N+](C1C=C(S(O[CH2:25][C@H:26]2[O:28][CH2:27]2)(=O)=O)C=CC=1)([O-])=O.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH2:25][C@H:26]1[O:28][CH2:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 15049327(S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropaneYield 84.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5 g (0.032 mol) of 2-amino-3-nitrophenol, 8 g (0.032 mol) of (S)-(+)-glycidyl 3-nitrobenzenesulfonate and 8.9 g of K2CO3 are mixed in 80 ml of acetone and the mixture is refluxed for 18 hours. Filtration is carried out, the solvent is evaporated under reduced pressure and the crude product is purified by flash chromatography, elution being carried out with a 7/3 cyclohexane/ethyl acetate mixture. The solid product obtained is triturated in ethyl ether and 5.67 g of the title product are obtained. M.p.: 107-109°. αD+28.1 (c=0.5%, MeOH).

Workup

  1. temperaturethe mixture is refluxed for 18 hours
  2. filtrationFiltration
  3. customthe solvent is evaporated under reduced pressure
  4. customthe crude product is purified by flash chromatography, elution
  5. customThe solid product obtained
  6. customis triturated in ethyl ether

Sources & evidence

ORD record
ord-f4b14f780c4148528ec5549cc4115d8e
Source dataset
uspto-grants-2005_02
Patent number
US06858629B1

Linked notes

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