Trifluoroacetic acid → HCID 86575138, compound

HRID 524464Notes

Reaction equation

HRID 524464 reaction equation
[CH3:1][C:2]([CH3:59])([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([CH3:56])[C@@H:28]2[CH2:27][CH2:26][C@H:25]2[C@@:20]3([CH3:55])[CH2:21][CH2:22][C@@:23]3(/[CH:40]=[CH:41]/[C:42]([NH:44][C:45]4([C:48]5[CH:53]=[CH:52][CH:51]=[C:50]([Cl:54])[CH:49]=5)[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([CH3:58])[CH3:57])=[O:12])[C:3]([O:5]C(C)(C)C)=[O:4].C(O)(C(F)(F)F)=O>ClCCl>[Cl:54][C:50]1[CH:49]=[C:48]([C:45]2([NH:44][C:42](=[O:43])/[CH:41]=[CH:40]/[C@:23]34[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:38])[CH3:39])=[C:24]3[C@@H:25]3[C@@:20]([CH3:55])([CH2:21][CH2:22]4)[C@@:19]4([CH3:56])[C@@H:28]([C@:29]5([CH3:32])[C@@H:16]([CH2:17][CH2:18]4)[C:15]([CH3:58])([CH3:57])[C@@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:1])([CH3:59])[C:3]([OH:5])=[O:4])[CH2:31][CH2:30]5)[CH2:27][CH2:26]3)[CH2:47][CH2:46]2)[CH:53]=[CH:52][CH:51]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89619473HCID 89619473, compound

Product 1

HCID 86575138HCID 86575138, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butyl 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-((1-(3-chlorophenyl)cyclopropyl)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, 0.241 mmol) in dichloromethane (5 mL) stirred at rt was added TFA (3 mL, 38.9 mmol). The reaction mixture was stirred at rt for 1 h. The mixture was evaporated to get the crude product which was purified by preparative-HPLC to get the product (100 mg, 53%) as a light white solid. 1H NMR (400 MHz, DMSO-d6) δ=12.18 (br. s., 1H), 8.78 (s, 1H), 7.38-7.18 (m, 2H), 7.13 (d, J=5.3 Hz, 1H), 7.08-6.96 (m, 1H), 6.65 (d, J=15.8 Hz, 1H), 5.92 (d, J=16.1 Hz, 1H), 4.39 (dd, J=4.8, 11.0 Hz, 1H), 3.31-3.08 (m, 1H), 2.85-2.72 (m, 1H), 2.63-0.58 (m, 53H); LC/MS: m/z calculated 773.4. Found 772.3 (M−1)−.

Workup

  1. customThe mixture was evaporated
  2. customto get the crude product which
  3. customwas purified by preparative-HPLC

Sources & evidence

ORD record
ord-81402ae3bc684484a3b1055c3097efd9
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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