Trifluoroacetic acid → HCID 71611455, compound

HRID 524475Notes

Reaction equation

HRID 524475 reaction equation
[CH3:1][C:2]([CH3:58])([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([CH3:55])[C@@H:28]2[CH2:27][CH2:26][C@H:25]2[C@@:20]3([CH3:54])[CH2:21][CH2:22][C@@:23]3(/[CH:40]=[CH:41]/[C:42]([NH:44][C@@H:45]([C:47]4[CH:52]=[CH:51][CH:50]=[C:49]([Cl:53])[CH:48]=4)[CH3:46])=[O:43])[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]32)[C:15]1([CH3:57])[CH3:56])=[O:12])[C:3]([O:5]C(C)(C)C)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:53][C:49]1[CH:48]=[C:47]([C@H:45]([NH:44][C:42](=[O:43])/[CH:41]=[CH:40]/[C@:23]23[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]2[C@@H:25]2[C@@:20]([CH3:54])([CH2:21][CH2:22]3)[C@@:19]3([CH3:55])[C@@H:28]([C@:29]4([CH3:32])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:56])([CH3:57])[C@@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:1])([CH3:58])[C:3]([OH:5])=[O:4])[CH2:31][CH2:30]4)[CH2:27][CH2:26]2)[CH3:46])[CH:52]=[CH:51][CH:50]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117701489HCID 117701489, compound

Product 1

HCID 71611455HCID 71611455, compoundYield 27%

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-(((R)-1-(3-chlorophenyl)ethyl)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 (400 mg, 0.489 mmol) in DCM (10 mL) that was stirred at room temp was then 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 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 (100 mg, 27%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.38-7.14 (m, 4H), 6.96 (d, J=15.8 Hz, 1H), 6.25 (d, J=7.8 Hz, 1H), 5.73 (d, J=15.6 Hz, 1H), 5.23-5.08 (m, 1H), 4.50 (dd, J=5.4, 10.7 Hz, 1H), 3.27-3.11 (m, 1H), 2.82-2.49 (m, 3H), 2.33-2.19 (m, 1H), 2.19-2.00 (m, 2H), 2.00-0.71 (m, 47H); LC/MS: m/z calculated 761.4. Found 762.2 (M+1)+.

Workup

  1. customThe mixture was evaporated to dryness
  2. additionthen diluted 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-d4b64c54434349a9b0b588d4a5e029a2
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

Loading…