Trifluoroacetic acid → HCID 71611586, compound

HRID 524477Notes

Reaction equation

HRID 524477 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]([NH:44][CH2:45][CH:46]4[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]4)=[O:43])[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>C(Cl)Cl>[CH:46]1([CH2:45][NH:44][C:42](=[O:43])/[CH:41]=[CH:40]/[C@:23]23[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:38])[CH3:39])=[C:24]2[C@@H:25]2[C@@:20]([CH3:52])([CH2:21][CH2:22]3)[C@@:19]3([CH3:53])[C@@H:28]([C@:29]4([CH3:32])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:54])([CH3:55])[C@@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:1])([CH3:56])[C:3]([OH:5])=[O:4])[CH2:31][CH2:30]4)[CH2:27][CH2:26]2)[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117701654HCID 117701654, compound

Product 1

HCID 71611586HCID 71611586, compoundYield 29.6%

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-((cyclohexylmethyl)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 (200 mg, 0.258 mmol) in DCM (10 mL) stirred at room temp was added TFA (5 mL, 64.9 mmol). The reaction mixture was stirred at 30° C. for 2 h. The product was evaporated to dryness and then diluted with 200 mL DCM. The organic phase was washed with saturated NaHCO3, water and brine. The organics were dried and concentrated under reduced pressure to afford crude product, which was purified by preparative-HPLC to afford the title compound (55 mg, 29%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=12.18 (br. s., 1H), 7.93 (t, J=5.8 Hz, 1H), 6.60 (d, J=15.8 Hz, 1H), 5.89 (d, J=15.8 Hz, 1H), 4.39 (dd, J=4.6, 11.2 Hz, 1H), 3.27-3.12 (m, 1H), 3.03-2.87 (m, 2H), 2.73 (dd, J=3.5, 11.8 Hz, 1H), 2.24-1.99 (m, 3H), 1.96-0.70 (m, 57H); LC/MS: m/z calculated 719.5. Found 720.5 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-c1624c5303b7437d9700c186d1c8fae9
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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