Hydrochloric Acid → HCID 66634950, compound

HRID 1473870Notes

Reaction equation

HRID 1473870 reaction equation
C(OC([NH:8][C@@H:9]([CH3:40])[C:10]([O:12][C@@H:13]1[CH2:29][C@@H:28]2[C@@:16]([CH3:39])([C@@H:17]3[C@@H:25]([CH2:26][CH2:27]2)[C@:24]2(O)[C@@:20]([CH3:38])([C@@H:21]([C:31]4[CH:32]=[CH:33][C:34](=[O:37])[O:35][CH:36]=4)[CH2:22][CH2:23]2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1)=[O:11])=O)(C)(C)C.Cl>CCOC(C)=O>[CH3:39][C@:16]12[CH2:15][CH2:14][C@H:13]([O:12][C:10](=[O:11])[C@@H:9]([NH2:8])[CH3:40])[CH2:29][C@H:28]1[CH2:27][CH2:26][C@@H:25]1[C@@H:17]2[CH2:18][CH2:19][C@@:20]2([CH3:38])[C:24]1=[CH:23][CH2:22][C@@H:21]2[C:31]1[CH:32]=[CH:33][C:34](=[O:37])[O:35][CH:36]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66611695HCID 66611695, compound

Product 1

HCID 66634950HCID 66634950, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl) hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl) 2-(tert-butoxy carbonylamino)propanoate (35 mg, 0.063 mmol, 1 eq) in EtOAc (3 mL) was added HCl (4 M in EtOAc, 3 mL) in drops at 0° C. The resulting mixture was warmed to room temperature after 30 min and stirred for 2 h. The mixture was quenched with saturated NaHCO3 solution and extracted with EtOAc (20 mL×3). The organic layer was washed with H2O (10 mL×4) and then dried over anhydrous Na2SO4, concentrated under reduced pressure. The crude product was then purified via Prep-TLC(CH2Cl2:MeOH=10:1) to afford the (S)-((3S,5R,8R,9S,10S,13R,17S)-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)-2-aminopropanoate. LCMS (M+H+) m/z 440.8.

Workup

  1. customThe mixture was quenched with saturated NaHCO3 solution
  2. extractionextracted with EtOAc (20 mL×3)
  3. washThe organic layer was washed with H2O (10 mL×4)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was then purified via Prep-TLC(CH2Cl2:MeOH=10:1)

Sources & evidence

ORD record
ord-96d9f562758142db99577ef9686218c9
Source dataset
uspto-grants-2015_04
Patent number
US09018197B2

Reaction notes

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