Sodium Hydroxide → HCID 86575596, compound

HRID 1401001Notes

Reaction equation

HRID 1401001 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]12[CH2:53][CH2:52][C@@H:51]([C:54]([CH3:56])=[CH2:55])[C@@H:10]1[C@@H:11]1[C@@:24]([CH3:27])([CH2:25][CH2:26]2)[C@@:23]2([CH3:28])[C@@H:14]([C@:15]3([CH3:50])[C@@H:20]([CH2:21][CH2:22]2)[C:19]([CH3:30])([CH3:29])[C:18]([C:31]2[CH2:49][C:33]4([CH2:36][C:35]([C:43]([O:45]C(C)C)=[O:44])([C:37]([O:39]C(C)C)=[O:38])[CH2:34]4)[CH:32]=2)=[CH:17][CH2:16]3)[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCOCC1.CO>[C:1]([O:5][C:6]([NH:8][C@:9]12[CH2:53][CH2:52][C@@H:51]([C:54]([CH3:56])=[CH2:55])[C@@H:10]1[C@@H:11]1[C@@:24]([CH3:27])([CH2:25][CH2:26]2)[C@@:23]2([CH3:28])[C@@H:14]([C@:15]3([CH3:50])[C@@H:20]([CH2:21][CH2:22]2)[C:19]([CH3:30])([CH3:29])[C:18]([C:31]2[CH2:49][C:33]4([CH2:36][C:35]([C:43]([OH:45])=[O:44])([C:37]([OH:39])=[O:38])[CH2:34]4)[CH:32]=2)=[CH:17][CH2:16]3)[CH2:13][CH2:12]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86692355HCID 86692355, compound

Product 1

HCID 86575596HCID 86575596, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of diisopropyl 6-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((tert-butoxycarbonyl)amino)-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]chrysen-9-yl)spiro[3.3]hept-5-ene-2,2-dicarboxylate (15 mg, 0.019 mmol) in dioxane (2 mL) and MeOH (1 mL) was added 1N NaOH (1 mL, 1 mmol). The mixture was stirred at 50° C. for 4 h. The solvent was removed in vacuo. The crude product was dissolved in dioxane (1 mL) and MeOH (1 mL). H2O was added dropwise, the solid formed was collected by filtration to give desired product in 88% yield. MS: m/e 688.6 (M−H)−, 2.72 min (method 5). 1H NMR (400 MHz, METHANOL-d4) δ 5.88 (s, 1H), 5.57-5.52 (m, 1H), 4.74 (d, J=1.8 Hz, 1H), 4.61 (s, 1H), 2.69 (s, 2H), 2.68-2.48 (m, 4H), 2.33-2.25 (m, 1H), 2.14 (dd, J=17.9, 6.7 Hz, 1H), 1.99-1.83 (m, 2H), 1.77-0.81 (m, 19H), 1.70 (s, 3H), 1.45 (s, 9H), 1.16 (s, 3H), 1.09 (s, 3H), 1.08 (s., 3H), 1.00 (s, 3H), 0.86 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe crude product was dissolved in dioxane (1 mL)
  3. additionH2O was added dropwise
  4. customthe solid formed
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-5f15f31e2b8048648a16062711f11191
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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