Trifluoroacetic acid → HCID 71611025, compound

HRID 524462Notes

Reaction equation

HRID 524462 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]=[CH:49][C:48]=4[Cl:53])[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>ClCCl>[Cl:53][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=1[C@H:45]([NH:44][C:42](=[O:43])/[CH:41]=[CH:40]/[C@:23]12[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]1[C@@H:25]1[C@@:20]([CH3:54])([CH2:21][CH2:22]2)[C@@:19]2([CH3:55])[C@@H:28]([C@:29]3([CH3:32])[C@@H:16]([CH2:17][CH2:18]2)[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]3)[CH2:27][CH2:26]1)[CH3:46]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117701504HCID 117701504, compound

Product 1

HCID 71611025HCID 71611025, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-tert-butyl 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-(((R)-1-(2-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 (200 mg, 0.101 mmol) in dichloromethane (6 mL) stirred at room temp was added TFA (3 ml, 38.9 mmol). The reaction mixture was stirred at 25° C. for 2 h. The product was extracted with DCM (20 mL*2) and the combined organic phase was washed with H2O (20 mL*2) and brine (30 mL), dried. Then, the solvent was removed under reduced pressure. The residue was purified by preparative-HPLC to give the title compound (70 mg, 0.092 mmol, 91%) was collected as white solid. 1H NMR (400 MHz, METHANOL-d4) δ=8.69 (d, J=7.3 Hz, 1H), 7.50-7.17 (m, 4H), 6.83 (d, J=16.1 Hz, 1H), 6.03 (d, J=15.8 Hz, 1H), 5.52-5.35 (m, 1H), 4.50 (dd, J=5.1, 11.2 Hz, 1H), 3.32-3.26 (m, 1H), 3.00-2.80 (m, 1H), 2.73-2.49 (m, 2H), 2.35-0.77 (m, 50H); LC/MS: m/z calculated 761.4. Found 762.3 (M+1)+.

Workup

  1. extractionThe product was extracted with DCM (20 mL*2)
  2. washthe combined organic phase was washed with H2O (20 mL*2) and brine (30 mL)
  3. customdried
  4. customThen, the solvent was removed under reduced pressure
  5. customThe residue was purified by preparative-HPLC

Sources & evidence

ORD record
ord-f7de837d028f471d866bfc9e2fab0b02
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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