Water → HCID 154041412, compound

HRID 453935Notes

Reaction equation

HRID 453935 reaction equation
[S:1](=[O:26])(=[O:25])([O:3][C:4]1[C:21]([O:22][CH3:23])=[CH:20][C:19]2[C@@H:18]3[C@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C:13](=O)[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=1)[NH2:2].Cl.[NH2:28][OH:29].C(=O)(O)[O-].[Na+].O>CO.C(OCC)(=O)C>[S:1](=[O:26])(=[O:25])([O:3][C:4]1[C:21]([O:22][CH3:23])=[CH:20][C:19]2[C@@H:18]3[C@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])/[C:13](=[N:28]/[OH:29])/[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=1)[NH2:2]

Participants

7

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 9842809HCID 9842809, compound

Product 1

HCID 154041412HCID 154041412, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 570 mg of 2-methoxy-17-oxo-estra-1,3,5(10)-trien-3-yl sulfamate, 365 mg of hydroxylamine hydrochloride and 441 mg of sodium bicarbonate in 8 ml of methanol was stirred under reflux for one hour. Then, it was mixed with 30 ml each of water and ethyl acetate. After phase separation, the aqueous phase was extracted twice more with 15 ml each of ethyl acetate. The combined organic phases were first washed with 15 ml of 0.5N HCl and then with saturated NaCl solution, dried on sodium sulfate and concentrated by evaporation in a rotary evaporator. The crude product was purified by flash chromatography (toluene/ethyl acetate 3:1). 444 mg (73%) of 2-methoxy-(E)-17-(oximino)-estra-1,3,5(10)-trien-3-yl sulfamate (17) was obtained as colorless crystals.

Workup

  1. temperatureunder reflux for one hour
  2. customAfter phase separation
  3. extractionthe aqueous phase was extracted twice more with 15 ml each of ethyl acetate
  4. washThe combined organic phases were first washed with 15 ml of 0.5N HCl
  5. dry with materialwith saturated NaCl solution, dried on sodium sulfate
  6. concentrationconcentrated by evaporation in a rotary evaporator
  7. customThe crude product was purified by flash chromatography (toluene/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-2d974e9c01214f9eba2c5fd6bb924a9f
Source dataset
uspto-grants-2013_07
Patent number
US08492570B2

Reaction notes

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