Trifluoroacetic acid → HCID 86575275, compound

HRID 524476Notes

Reaction equation

HRID 524476 reaction equation
[CH3:1][C:2]([CH3:52])([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([CH3:49])[C@@H:28]2[CH2:27][CH2:26][C@H:25]2[C@@:20]3([CH3:48])[CH2:21][CH2:22][C@@:23]3(/[CH:40]=[CH:41]/[C:42]([NH:44][CH2:45][CH2:46][OH:47])=[O:43])[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]32)[C:15]1([CH3:51])[CH3:50])=[O:12])[C:3]([O:5]C(C)(C)C)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:47][CH2:46][CH2:45][NH:44][C:42](=[O:43])/[CH:41]=[CH:40]/[C@:23]12[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:38])[CH3:39])=[C:24]1[C@@H:25]1[C@@:20]([CH3:48])([CH2:21][CH2:22]2)[C@@:19]2([CH3:49])[C@@H:28]([C@:29]3([CH3:32])[C@@H:16]([CH2:17][CH2:18]2)[C:15]([CH3:50])([CH3:51])[C@@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:1])([CH3:52])[C:3]([OH:5])=[O:4])[CH2:31][CH2:30]3)[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117701510HCID 117701510, compound

Product 1

HCID 86575275HCID 86575275, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 1-tert-butyl 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-((2-hydroxyethyl)amino)-3-oxoprop-1-en-1-yl)-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) 2,2-dimethylsuccinate (60 mg, 0.083 mmol) in DCM (5 mL) stirred at room temp was added TFA (2.5 mL, 32.4 mmol). The reaction mixture was stirred at 30° C. for 2 h. The reaction was evaporated to dryness then diluted with 200 mL DCM. The organic phase was washed with saturated NaHCO3 solution (200 mL*3), water and brine. The organics were dried and concentrated under reduced pressure to afford crude product which was further purified by preparative-HPLC to afford the title compound (35 mg, 63%) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ=6.85 (d, J=16.1 Hz, 1H), 5.96 (d, J=16.1 Hz, 1H), 4.49 (dd, J=5.5, 10.5 Hz, 1H), 3.64 (t, J=5.6 Hz, 2H), 3.39 (t, J=5.6 Hz, 2H), 3.37-3.21 (m, 1H), 2.91 (dd, J=4.1, 11.7 Hz, 0H), 2.68-2.50 (m, 2H), 2.33-2.10 (m, 3H), 2.09-0.75 (m, 44H).

Workup

  1. customThe reaction was evaporated to dryness
  2. additionthen diluted with 200 mL DCM
  3. washThe organic phase was washed with saturated NaHCO3 solution (200 mL*3), water and brine
  4. customThe organics were dried
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude product which
  7. customwas further purified by preparative-HPLC

Sources & evidence

ORD record
ord-e03d65fe9a30438e900e36b5980fcdf8
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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