Hydrochloric Acid → HCID 54437758, compound

HRID 1065705Notes

Reaction equation

HRID 1065705 reaction equation
C([O:4][C:5]1[CH:22]=[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]([NH:23][C:24](=[O:27])[CH2:25][CH3:26])[C@H:13]([O:28]C(=O)C)[CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=O)C.[OH-].[Na+].O.Cl>C(O)C>[CH3:26][CH2:25][C:24]([NH:23][C@H:14]1[C@H:13]([OH:28])[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]=[CH:22][C:5]([OH:4])=[CH:6][C:7]=1[CH2:8][CH2:9]3)=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 54367091HCID 54367091, compound

Product 1

HCID 54437758HCID 54437758, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

17β-Methylacetamido-oestra-1,3,5(10)-triene-3,16α-diol diacetate (19.7 g) was dissolved in ethanol (394 ml) and sodium hydroxide (50.9 ml; 2 N) was added. The resulting solution was refluxed for 1 h., cooled to room temperature and water (4 l) was added. The mixture was acidified with hydrochloric acid (2 N) and the precipitated product was filtered off and washed with water. Crystallisation from methanol-ether gave an isomeric mixture of 17β-methylacetamido-oestra-1,3,5(10)-triene-3,16α-diols (13.1 g; 83%).

Workup

  1. temperatureThe resulting solution was refluxed for 1 h.
  2. filtrationthe precipitated product was filtered off
  3. washwashed with water
  4. customCrystallisation from methanol-ether
  5. customgave

Sources & evidence

ORD record
ord-92d1f7f33ef04d549e2c07d3ed3494c0
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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