2-(O-aminooxy)ethylamine dihydrochloride → HCID 87574026, compound

HRID 1182864Notes

Reaction equation

HRID 1182864 reaction equation
[CH2:1]([C@H:3]1[C:20](=O)[CH2:19][CH2:18][C@@:17]2([CH3:22])[CH:4]1[C:5](=[O:24])[CH2:6][C@@H:7]1[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]1[CH2:9][CH2:10][C:11]2=[O:23])[CH3:2].[ClH:25].Cl.[NH2:27][CH2:28][CH2:29][O:30][NH2:31]>C1COCC1.O>[ClH:25].[NH2:27][CH2:28][CH2:29][O:30]/[N:31]=[C:20]1/[C@H:3]([CH2:1][CH3:2])[CH:4]2[C@:17]([CH3:22])([CH2:18][CH2:19]/1)[C@@H:16]1[C@H:7]([C@H:8]3[C@@:12]([CH2:14][CH2:15]1)([CH3:13])[C:11](=[O:23])[CH2:10][CH2:9]3)[CH2:6][C:5]2=[O:24]

Participants

5

Reactant 2

HCID 143623262-(O-aminooxy)ethylamine dihydrochlorideHCID 68728543HCID 68728543, compound

Product 1

HCID 87574026HCID 87574026, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4β-ethylandrostan-3,6,17-trione (Preparation 11, 67 mg) in THF (1.1 ml), a solution of 2-aminoethoxyamine dihydrochloride (31 mg) and Na2HPO4.12H2O (15 mg) in H2O (0.55 ml) was added in portions over 45 minutes. After 3.5 h, the solution was evaporated, water was added and the aqueous phase was extracted with THF. The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated to dryness. The crude product was triturated with Et2O and the precipitate was filtered to give the title compound I-bd (34 mg, 42%).

Workup

  1. customthe solution was evaporated
  2. additionwater was added
  3. extractionthe aqueous phase was extracted with THF
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customThe crude product was triturated with Et2O
  8. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-8b14f3effac341d181ed03acc8da3373
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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