Hydrochloric Acid → 3alpha-Hydroxy-11-hydroxyimino-5alpha-androstane-17beta-carboxylic acid

HRID 223433Notes

Reaction equation

HRID 223433 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].[OH:6][C@@H:7]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:21]2[C:20](=O)[CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:27]([OH:29])=[O:28])[CH2:8]1.Cl>C(O)C.O>[OH:6][C@@H:7]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:21]2[C:20](=[N:2][OH:3])[CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:27]([OH:29])=[O:28])[CH2:8]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 227882653alpha-Hydroxy-5alpha-androstan-11-one 17beta-carboxylic acid

Product 1

HCID 867385953alpha-Hydroxy-11-hydroxyimino-5alpha-androstane-17beta-carboxylic acidYield 63.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Hydroxylamine hydrochloride (4 g) was added to a water cooled solution of sodium hydroxide (50%; 16 ml). This mixture was added to a solution of 3α-hydroxy-11-oxo-5α-androstane-17β-carboxylic acid (1.5 g) in ethanol (70 ml). The mixture was heated at reflux for 24 h, cooled and brought to pH 1 with concentrated HCl solution. Water (800 ml) was added and the precipitate (1.42 g) was collected by filtration, washed with water (2×300 ml) and dried. Crystallisation from ethyl acetate gave the title compound (1 g) m.p. 250°-253° C. (dec) [α]D +124° (EtOH C=1%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h
  3. temperaturecooled
  4. filtrationthe precipitate (1.42 g) was collected by filtration
  5. washwashed with water (2×300 ml)
  6. customdried
  7. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-c5a1cc07a0d8496db98d4f3d483eb501
Source dataset
uspto-grants-1982_10
Patent number
US04353898

Reaction notes

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