Acetic Acid → HCID 70616124, compound

HRID 839521Notes

Reaction equation

HRID 839521 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH2:23][O:24]C(=O)C)[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@:11]3([OH:35])[CH2:12][CH2:13][C@@H:14]2[O:28]C(=O)C(C)(C)C)[CH2:6]1)(=O)C.[OH-].[K+].C(O)(=O)C>C(OCC)(=O)C>[OH:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH2:23][OH:24])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@:11]3([OH:35])[CH2:12][CH2:13][C@@H:14]2[OH:28])[CH2:6]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 22803789HCID 22803789, compound

Product 1

HCID 70616124HCID 70616124, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of 30 mg of 3β ,19-diacetoxy-14β-hydroxy-17β-pivaloxy-5α-androstane and 3.0 ml of 0.2 N methanolic potassium hydroxide was heated at 70° C. for 16 hours under nitrogen whereupon the mixture was neutralized with 0.2 N glacial acetic acid in ethyl acetate and evaporated to dryness at reduced pressure. The residue obtained was treated with ethyl acetate and filtered through diatomaceous earth. Evaporation of the filtrate yielded 3β ,14β ,17β ,19-tetrahydroxy-5α-androstane as indicated by tlc analysis.

Workup

  1. customevaporated to dryness at reduced pressure
  2. customThe residue obtained
  3. filtrationfiltered through diatomaceous earth
  4. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-b4d0c79b600b442aa7432348f47b48a3
Source dataset
uspto-grants-1978_06
Patent number
US04096142

Reaction notes

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