Water → HCID 86690376, compound

HRID 513888Notes

Reaction equation

HRID 513888 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([CH3:42])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:41])[CH2:12][CH2:13][C@@:14]3([CH2:31][CH2:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:26][C:25](=[O:27])[C:24]([CH:28]([CH3:30])[CH3:29])=[C:15]32)[C:6]1([CH3:44])[CH3:43])(=O)C.[OH-].[Na+].O.CCOC(C)=O>CO.C1COCC1>[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([CH3:42])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:41])[CH2:12][CH2:13][C@@:14]3([CH2:31][CH2:32][NH:33][C:34](=[O:35])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:26][C:25](=[O:27])[C:24]([CH:28]([CH3:30])[CH3:29])=[C:15]32)[C:6]1([CH3:43])[CH3:44]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86690377HCID 86690377, compound

Product 1

HCID 86690376HCID 86690376, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-((tert-butoxycarbonyl)amino)ethyl)-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-9-yl acetate (35) (5.8 g, 9.48 mmol), NaOH (11.37 g, 284 mmol) in methanol (4 mL), THF (6 mL), and Water (2 mL) was stirred at room temperature for 1 h. EtOAc was added and the reaction mixture was washed with water. The organic layer was separated, washed with water and brine, and dried (Na2SO4). Removal of the solvent provide tert-butyl (2-((3aR,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)ethyl)carbamate (36) (5.4 g, 7.87 mmol, 83% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ=4.53-4.36 (m, 1H), 3.30-2.94 (m, 4H), 2.94-2.67 (m, 2H), 2.28 (d, J=18.8 Hz, 1H), 2.11-0.55 (m, 50H); LC/MS: m/z calculated 569.4. found 592.3 (M+Na)+.

Workup

  1. washthe reaction mixture was washed with water
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-d2a4c26dfbb049c192b08c8a34d7395a
Source dataset
uspto-grants-2015_08
Patent number
US09102685B2

Reaction notes

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