Tetrabutylammonium Fluoride → HCID 67775281, compound

HRID 2405516Notes

Reaction equation

HRID 2405516 reaction equation
[CH:1]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([C:45](=[O:58])[NH:46][CH2:47][CH2:48][C:49](=[O:57])[O:50]CC[Si](C)(C)C)[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:44])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[CH:16]([C:29]1[CH:43]=[CH:42][C:32]([C:33]([O:35]CC[Si](C)(C)C)=[O:34])=[CH:31][CH:30]=1)[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:49]([CH2:48][CH2:47][NH:46][C:45]([C@:7]12[CH2:6][CH2:5][C@@H:4]([CH:1]([CH3:3])[CH3:2])[C@@H:8]1[C@@H:9]1[C@@:22]([CH3:25])([CH2:23][CH2:24]2)[C@@:21]2([CH3:26])[C@@H:12]([C@:13]3([CH3:44])[C@@H:18]([CH2:19][CH2:20]2)[C:17]([CH3:28])([CH3:27])[CH:16]([C:29]2[CH:43]=[CH:42][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)=[O:58])([OH:57])=[O:50]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67774463HCID 67774463, compound

Product 1

HCID 67775281HCID 67775281, compoundYield 52,882.398%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(trimethylsilyl)ethyl 4-((1S,3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bR)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3a-(3-oxo-3-(2-(trimethylsilyl)ethoxy)propylcarbamoyl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (14 mg, 0.017 mmol) was dissolved in THF (Volume: 0.5 mL) and treated with TBAF (0.5 mL, 0.500 mmol). The mixture was stirred at rt for 1 h. The solvent was removed in vacuo and the residue was dissolved in DMF and purified using reverse phase prep HPLC to afford 4-((1S,3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bR)-3a-(2-carboxyethylcarbamoyl)-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid (6 mg, 8.99 mmol, 53.6% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.82 (d, J=8.28 Hz, 2H), 7.56 (t, J=5.52 Hz, 1H), 7.29 (d, J=8.28 Hz, 2H), 3.37-3.11 (m, 2H), 2.65-2.56 (m, 1H), 2.47-2.39 (m, 1H), 2.39-2.31 (m, 2H), 2.28-2.18 (m, 1H), 2.18-2.08 (m, 2H), 1.84-0.97 (m, 22H), 0.94 (s, 6H), 0.91 (s, 3H), 0.83 (d, J=6.78 Hz, 3H), 0.74 (d, J=6.78 Hz, 3H), 0.72 (s, 3H), 0.67 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in DMF
  3. custompurified

Sources & evidence

ORD record
ord-e82ea77b72614690bd893cc0a8d0abe0
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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