Hydrochloric Acid → (4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-5-Hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one hydrochloride

HRID 446834Notes

Reaction equation

HRID 446834 reaction equation
[ClH:1].F[C@@:3]12[C@:16]3([CH3:17])[C:11](=[CH:12][C:13](=[O:18])[CH:14]=[CH:15]3)[C@@H:10](F)[CH2:9][C@H:8]1[C@@H:7]1[CH2:20][C@@H:21]3[C@:25]([C:26](=[O:32])[CH2:27][O:28]C(=O)C)([C@@:6]1([CH3:33])[CH2:5][C@@H:4]2[OH:34])[CH2:24][NH:23][CH2:22]3.Cl>CO.O1CCOCC1>[ClH:1].[OH:34][C@@H:4]1[C@H:3]2[C@@H:8]([CH2:9][CH2:10][C:11]3[C@:16]2([CH3:17])[CH:15]=[CH:14][C:13](=[O:18])[CH:12]=3)[C@@H:7]2[CH2:20][C@@H:21]3[C@:25]([C:26](=[O:32])[CH2:27][OH:28])([C@@:6]2([CH3:33])[CH2:5]1)[CH2:24][NH:23][CH2:22]3

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 67353702Acetic acid 2-((4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4-aH-8-aza-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl ester hydrochloride

Product 1

HCID 67351491(4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-5-Hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one hydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

In a closed vessel compound 20 (300 mg, 0.600 mmol) is dissolved in MeOH, HCl (0.045 ml, 0.180 mmol) in dioxane is added and the mixture is stirred at room temperature for 10 days, then further HCl (0.045 ml, 0.180 mmol) is added and the reaction mixture is stirred for further 2 days. The reaction mixture is concentrated to dryness affording the title compound (253 mg, 0.600 mmol, 100% yield).

Workup

  1. stirringthe reaction mixture is stirred for further 2 days
  2. concentrationThe reaction mixture is concentrated to dryness

Sources & evidence

ORD record
ord-9bf8c21e35034e10a09c8b80b590eccf
Source dataset
uspto-grants-2013_07
Patent number
US08481517B2

Reaction notes

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