Sodium Hydroxide → (E)-3-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-3a-yl)acrylic acid

HRID 524445Notes

Reaction equation

HRID 524445 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:39])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:38])[CH2:12][CH2:13][C@@:14]3(/[CH:31]=[CH:32]/[C:33]([O:35]CC)=[O:34])[CH2:26][C:25](=[O:27])[C:24]([CH:28]([CH3:30])[CH3:29])=[C:15]32)[C:6]1([CH3:41])[CH3:40])(=O)C.[OH-].[Na+]>O1CCCC1.CO.O>[OH:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:39])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:38])[CH2:12][CH2:13][C@@:14]3(/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34])[CH2:26][C:25](=[O:27])[C:24]([CH:28]([CH3:30])[CH3:29])=[C:15]32)[C:6]1([CH3:41])[CH3:40]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 117718748(E)-ethyl 3-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-acetoxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-3a-yl)acrylate

Product 1

HCID 89661781(E)-3-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-3a-yl)acrylic acidYield 71.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of (E)-ethyl 3-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-acetoxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-3a-yl)acrylate (1.6 g, 2.82 mmol) in tetrahydrofuran (THF) (15 mL), methanol (10 mL) and water (5 mL) was added sodium hydroxide (4.52 g, 113 mmol). The reaction mixture was stirred at 20° C. for 4 hs. The reaction mixture was evaporated to dryness and adjusted pH to 5 by saturated NH4Cl. The solid is solved into DCM (50 mL), washed with water, dried over Na2SO4 and concentrated to yield the (E)-3-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-3a-yl)acrylic acid (1.2 g, 2.012 mmol, 71.3%) as a yellow solid.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e9425dc38a3e4e86b39970f7355c1127
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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