Trifluoroacetic acid → HCID 86575261, compound

HRID 524474Notes

Reaction equation

HRID 524474 reaction equation
[CH3:1][C:2]([CH3:55])([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([CH3:52])[C@@H:28]2[CH2:27][CH2:26][C@H:25]2[C@@:20]3([CH3:51])[CH2:21][CH2:22][C@@:23]3(/[CH:40]=[CH:41]/[C:42]([NH:44][CH:45]4[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]4)=[O:43])[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]32)[C:15]1([CH3:54])[CH3:53])=[O:12])[C:3]([O:5]C(C)(C)C)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:45]1([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]([CH3:51])([CH2:21][CH2:22]3)[C@@:19]3([CH3:52])[C@@H:28]([C@:29]4([CH3:32])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:54])([CH3:53])[C@@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:1])([CH3:55])[C:3]([OH:5])=[O:4])[CH2:31][CH2:30]4)[CH2:27][CH2:26]2)[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89619765HCID 89619765, compound

Product 1

HCID 86575261HCID 86575261, compoundYield 32.4%

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-(cyclohexylamino)-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 (400 mg, 0.525 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 mixture was evaporated to dryness, then diluted by 200 mL DCM. The organic phase was washed with saturated NaHCO3 solution, water and saturated brine, dried and concentrated under reduced pressure to afford crude product. This material was further purified by preparative-HPLC to afford the title compound (120 mg, 32%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ=6.92 (d, J=15.8 Hz, 1H), 5.62 (d, J=15.8 Hz, 1H), 5.37 (d, J=8.3 Hz, 1H), 4.50 (dd, J=5.3, 11.0 Hz, 1H), 3.94-3.73 (m, 1H), 3.27-3.14 (m, 2H), 2.80-2.51 (m, 3H), 2.37-2.03 (m, 3H), 2.03-0.69 (m, 54H); LC/MS: m/z calculated 705.5. Found 706.3 (M+1)+.

Workup

  1. customThe mixture was evaporated to dryness
  2. additiondiluted by 200 mL DCM
  3. washThe organic phase was washed with saturated NaHCO3 solution, water and saturated brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude product
  7. customThis material was further purified by preparative-HPLC

Sources & evidence

ORD record
ord-f1f21a786c15406f88954fe0e420551b
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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