Trifluoroacetic acid → HCID 86575087, compound

HRID 524461Notes

Reaction equation

HRID 524461 reaction equation
[CH3:1][C:2]([CH3:56])([CH2:10][C:11]([O:13][C@H:14]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@@H:16]([CH2:17][CH2:18][C@:19]3([CH3:53])[C@@H:28]2[CH2:27][CH2:26][C@H:25]2[C@@:20]3([CH3:52])[CH2:21][CH2:22][C@@:23]3(/[CH:40]=[CH:41]/[C:42](=[O:51])[NH:43][C:44]4[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=4)[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]32)[C:15]1([CH3:55])[CH3:54])=[O:12])[C:3]([O:5]C(C)(C)C)=[O:4].C(O)(C(F)(F)F)=O>ClCCl>[CH:37]([C:33]1[C:34](=[O:36])[CH2:35][C@:23]2(/[CH:40]=[CH:41]/[C:42](=[O:51])[NH:43][C:44]3[CH:45]=[CH:46][C:47]([CH3:50])=[CH:48][CH:49]=3)[CH2:22][CH2:21][C@:20]3([CH3:52])[C@H:25]([CH2:26][CH2:27][C@H:28]4[C@@:19]3([CH3:53])[CH2:18][CH2:17][C@@H:16]3[C@:29]4([CH3:32])[CH2:30][CH2:31][C@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:56])([CH3:1])[C:3]([OH:5])=[O:4])[C:15]3([CH3:54])[CH3:55])[C:24]=12)([CH3:39])[CH3:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117701706HCID 117701706, compound

Product 1

HCID 86575087HCID 86575087, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butyl 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3a-((E)-3-oxo-3-(p-tolylamino)prop-1-en-1-yl)-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) 2,2-dimethylsuccinate (250 mg, 0.325 mmol) in dichloromethane (5 mL) stirred at rt was added TFA (0.025 mL, 0.325 mmol). The reaction mixture was stirred at rt for 1 h. Upon completion and work-up and purification the title compound was obtained as a trifluoroacetic acid salt (150 mg, 0.181 mmol, 55.8%) as a light white solid. 1H NMR (300 MHz, DMSO-d6) δ=9.70 (s, 1H), 7.51 (d, J=8.4 Hz, 2H), 7.11 (d, J=8.4 Hz, 2H), 6.83 (d, J=15.8 Hz, 1H), 6.08 (d, J=15.7 Hz, 1H), 4.53-4.32 (m, 1H), 3.30-3.11 (m, 1H), 2.90-2.73 (m, 1H), 2.55-2.51 (m, 1H), 2.35-0.75 (m, 51H); LC/MS: m/z calculated 713.5. Found 714.3 (M+1)+.

Workup

  1. customUpon completion and work-up and purification the title compound

Sources & evidence

ORD record
ord-83c3b8e5451f44ceb058295e49863b6a
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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