Sodium Hydroxide → HCID 68357880, compound

HRID 85668Notes

Reaction equation

HRID 85668 reaction equation
[C:1]([N:4]([CH2:44][CH2:45][N:46]1[CH2:51][CH2:50][S:49](=[O:53])(=[O:52])[CH2:48][CH2:47]1)[C@:5]12[CH2:40][CH2:39][C@@H:38]([C:41]([CH3:43])=[CH2:42])[C@@H:6]1[C@@H:7]1[C@@:20]([CH3:23])([CH2:21][CH2:22]2)[C@@:19]2([CH3:24])[C@@H:10]([C@:11]3([CH3:37])[C@@H:16]([CH2:17][CH2:18]2)[C:15]([CH3:26])([CH3:25])[C:14]([C:27]2[CH:36]=[CH:35][C:30]([C:31]([O:33]C)=[O:32])=[CH:29][CH:28]=2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)(=[O:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[C:1]([N:4]([CH2:44][CH2:45][N:46]1[CH2:51][CH2:50][S:49](=[O:52])(=[O:53])[CH2:48][CH2:47]1)[C@:5]12[CH2:40][CH2:39][C@@H:38]([C:41]([CH3:43])=[CH2:42])[C@@H:6]1[C@@H:7]1[C@@:20]([CH3:23])([CH2:21][CH2:22]2)[C@@:19]2([CH3:24])[C@@H:10]([C@:11]3([CH3:37])[C@@H:16]([CH2:17][CH2:18]2)[C:15]([CH3:25])([CH3:26])[C:14]([C:27]2[CH:28]=[CH:29][C:30]([C:31]([OH:33])=[O:32])=[CH:35][CH:36]=2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86676610HCID 86676610, compound

Product 1

HCID 68357880HCID 68357880, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(acetyl(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)amino)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-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)benzoate (40 mg, 0.054 mmol) in 1,4-dioxane (1 mL) was added NaOH (1N) (0.27 mL, 0.27 mmol). The mixture was stirred at rt for 16.5 h then was purified directly by prep HPLC. The fractions containing the expected product were combined and concentrated under reduced pressure to give 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(acetyl(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)amino)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-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)benzoic acid (14 mg, 0.018 mmol, 33%) as a white solid. LCMS: m/e 733.5 (M+H)+, 1.96 min (method 2). 1H NMR (400 MHz, Chloroform-d) δ=7.99 (d, J=7.8 Hz, 2H), 7.22 (d, J=7.8 Hz, 2H), 5.23 (d, J=4.0 Hz, 1H), 4.85 (br. s., 1H), 4.68 (br. s., 1H), 3.65 (br. s., 2H), 3.40-3.04 (m, 8H), 2.97-2.46 (m, 4H), 1.74 (s, 3H), 1.27 (s, 3H), 1.03-0.98 (m, 9H), 0.95 (br. s., 3H), 0.89 (br. s., 3H), 2.20-0.71 (m, 21H).

Workup

  1. customthen was purified directly by prep HPLC
  2. additionThe fractions containing the expected product
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2933d11319da4dd99c51a0dc1537bef0
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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