Sodium Hydroxide → HCID 88124666, compound

HRID 1416525Notes

Reaction equation

HRID 1416525 reaction equation
[CH:1]([CH:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C@@H:5]([C@@H:6]([OH:23])[CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[OH:22])[CH2:4]1)=O.[OH-].[Na+].Cl.Cl.[NH2:28][CH2:29][CH2:30][O:31][NH2:32]>O1CCOCC1.O.O>[NH2:28][CH2:29][CH2:30][O:31]/[N:32]=[CH:1]\[C@H:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C@@H:5]([C@@H:6]([OH:23])[CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[OH:22])[CH2:4]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 143623262-(O-aminooxy)ethylamine dihydrochlorideHCID 15838430HCID 15838430, compound

Product 1

HCID 88124666HCID 88124666, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of 3-formyl-5α-androstan-6α,17β-diol (II-c, Prep. 3, 240 mg) in dioxane/water (2/1, 30 mL) was treated with sodium hydroxide (0.1 N) to pH=13-14 and stirred for 15 minutes, then a solution O-(2-aminoethyl)-hydroxylamine dihydrochloride (170 mg) in water (3 mL) was poured in. After 1 hr. the organic solvent was distilled off and the acqueous solution was extracted with chloroform (5×20 mL). The combined organic layers were dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography (SiO2, chloroform/methanol/ammonia 90/10/1) to give (Z)-3β-(2-aminoethoxyiminomethyl)-5α-androstan-6α,17β-diol, which was dissolved in ethyl acetate/methanol 70/30 and treated with oxalic acid to give 85 mg of (Z)-3β-(2-aminoethoxyiminomethyl)-5α-androstan-6α,17β-diol oxalate (I-d) as a white solid mp 190-192° C.

Workup

  1. waitAfter 1 hr
  2. distillationthe organic solvent was distilled off
  3. extractionthe acqueous solution was extracted with chloroform (5×20 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was purified by flash chromatography (SiO2, chloroform/methanol/ammonia 90/10/1)

Sources & evidence

ORD record
ord-8d47019e1c754c83b19de591a042c239
Source dataset
uspto-grants-1999_06
Patent number
US05914324

Reaction notes

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