Hydrochloric Acid → HCID 86731493, compound

HRID 1773035Notes

Reaction equation

HRID 1773035 reaction equation
C([O:3][C:4](=[O:46])/[CH:5]=[CH:6]/[C:7]1[C:8]([CH3:45])([CH3:44])[C@H:9]2[C@:22]([CH3:25])([CH2:23][CH:24]=1)[CH:21]1[C@:12]([CH3:43])([C@@:13]3([CH3:42])[C@H:18]([CH2:19][CH2:20]1)[C@H:17]1[C@H:26]([C:29]([CH3:31])=[CH2:30])[CH2:27][CH2:28][C@:16]1([C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH2:15][CH2:14]3)[CH2:11][CH2:10]2)C.[OH-].[Na+].Cl>O1CCOCC1.O>[CH2:35]([O:34][C:32]([C@:16]12[CH2:28][CH2:27][C@@H:26]([C:29]([CH3:31])=[CH2:30])[C@@H:17]1[C@@H:18]1[C@@:13]([CH3:42])([CH2:14][CH2:15]2)[C@@:12]2([CH3:43])[CH:21]([C@:22]3([CH3:25])[C@@H:9]([CH2:10][CH2:11]2)[C:8]([CH3:45])([CH3:44])[C:7](/[CH:6]=[CH:5]/[C:4]([OH:46])=[O:3])=[CH:24][CH2:23]3)[CH2:20][CH2:19]1)=[O:33])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86731492(1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-benzyl 9-((E)-3-ethoxy-3-oxoprop-1-enyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate

Product 1

HCID 86731493HCID 86731493, compoundYield 105%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-benzyl 9-((E)-3-ethoxy-3-oxoprop-1-enyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate (20 mg, 0.032 mmol) and 10 N sodium hydroxide (0.032 mL, 0.319 mmol) in dioxane (0.5 mL) and water (0.5 mL) was heated at 100° C. for 3 hours. The reaction mixture was neutralized with 1N HCl to pH=6 and extracted with ethyl acetate (3×4 mL). The extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the title compound (20 mg, 105%). This material was used in the next step without further purification. LCMS: m/e 597.68 (M−H)−, 2.50 min (method 6).

Workup

  1. extractionextracted with ethyl acetate (3×4 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ab7a39c5e504f02b0a6de21d88708f6
Source dataset
uspto-grants-2016_02
Patent number
US09249180B2

Reaction notes

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