Hydroxyamine hydrochloride → HCID 86759351, compound

HRID 2121349Notes

Reaction equation

HRID 2121349 reaction equation
C([O:4][C:5]1[C:22]([O:23][CH2:24][CH3:25])=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C@@H:14]([O:26][C:27](=[O:29])[CH3:28])[CH2:13][CH2:12]4)[CH2:9][C:8](=O)[C:7]=2[CH:6]=1)(=O)C.Cl.[NH2:32][OH:33]>N1C=CC=CC=1>[C:27]([O:26][C@H:14]1[CH2:13][CH2:12][C@H:11]2[C@H:10]3[C@H:19]([CH2:18][CH2:17][C@:15]12[CH3:16])[C:20]1[CH:21]=[C:22]([O:23][CH2:24][CH3:25])[C:5]([OH:4])=[CH:6][C:7]=1[C:8](=[N:32][OH:33])[CH2:9]3)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 11796064HCID 11796064, compound

Product 1

HCID 86759351HCID 86759351, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3,17,β-diacetoxy-2-ethoxy-estra-1,3,5(10)-triene-6-one (5, 800 mg, 1.93 mmol) in pyridine (12 ml) was treated with hydroxylamine hydrochloride (1.07 g, 15.4 mmol). The resulting mixture was stirred and heated at 100° C. for 30 min. The mixture was cooled to room temperature and then poured into ice/water mixture (150 ml). The compound was extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with sodium bicarbonate (100 ml), water (2×100 ml) and brine (2×100 ml), dried over sodium sulfate, and evaporated to dryness. Chromatography of the residue on silica gel using 30% ethyl acetate in hexane gave the title compound (763 mg, 89%), which was crystallized from ethyl acetate/hexane to afford title compound 27 as yellowish crystals: mp 226-227° C. 1H NMR (CDCl3) δ7.55 (s, 1 H). 6.78 (s, 1 H), 4.75 (t, J=8.5 Hz, 1 H), 4.19 (q, J=6.9 Hz, 2 H), 3.15 (dd, J=4.3 and 12 Hz, 1 H), 1.2-2.40 (m, 18 H), 0.85 (s, 3 H); CIMS (isobutane) m/z (rel intensity) 388 (MH+, 100), 372 (MH—H2O, 10), 328 (75); Anal. Calcd for C22H29O5N: C, 68.20; H, 7.54; N, 3.61. Found: C, 68.04; H, 7.62; N, 3.54.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe compound was extracted with ethyl acetate (3×100 ml)
  3. washThe combined organic layers were washed with sodium bicarbonate (100 ml), water (2×100 ml) and brine (2×100 ml)
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-af14430c03524854af5c93311bd4818f
Source dataset
uspto-grants-2004_02
Patent number
US06696436B1

Reaction notes

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