Trifluoroacetic acid → Trifluoroacetic acid

HRID 524458Notes

Reaction equation

HRID 524458 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][C:45]4[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][N:46]=4)=[O:43])[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]32)[C:15]1([CH3:55])[CH3:54])=[O:12])[C:3]([O:5]C(C)(C)C)=[O:4].[C:57]([OH:63])([C:59]([F:62])([F:61])[F:60])=[O:58]>ClCCl>[Cl:51][C:48]1[CH:49]=[CH:50][C: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)=[N:46][CH:47]=1.[C:57]([OH:63])([C:59]([F:62])([F:61])[F:60])=[O:58]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117701509HCID 117701509, compound

Product 2

HCID 6422Trifluoroacetic acidYield 417.6%HCID 89641077HCID 89641077, compound

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-((5-chloropyridin-2-yl)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 (100 mg, 0.126 mmol) in dichloromethane (4 mL) stirred at rt was added TFA (2 mL, 26.0 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 give the title compound as a TFA salt (60 mg, 55.9%). 1H NMR (400 MHz, CHLOROFORM-d) δ=11.06 (br. s., 1H), 8.54 (d, J=9.0 Hz, 1H), 8.13 (d, J=2.3 Hz, 1H), 7.83 (dd, J=2.3, 9.0 Hz, 1H), 7.10 (d, J=15.8 Hz, 1H), 6.09 (d, J=15.8 Hz, 1H), 4.52 (dd, J=4.3, 11.5 Hz, 1H), 3.30-3.12 (m, 1H), 2.82-2.52 (m, 3H), 2.38-2.08 (m, 3H), 2.04-1.75 (m, 3H), 1.75-0.60 (m, 41H); LC/MS: m/z calculated 734.4. Found 735.3 (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-520e701c74ea47f6966dd2d0b23476e4
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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