Trifluoroacetic acid → Trifluoroacetic acid

HRID 524453Notes

Reaction equation

HRID 524453 reaction equation
[CH3:1][C:2]([CH3:57])([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([CH3:54])[C@@H:28]2[CH2:27][CH2:26][C@H:25]2[C@@:20]3([CH3:53])[CH2:21][CH2:22][C@@:23]3(/[CH:40]=[CH:41]/[C:42](=[O:52])[NH:43][C@@H:44]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=4)[CH3:45])[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]32)[C:15]1([CH3:56])[CH3:55])=[O:12])[C:3]([O:5]C(C)(C)C)=[O:4].[C:58]([OH:64])([C:60]([F:63])([F:62])[F:61])=[O:59]>ClCCl>[CH:37]([C:33]1[C:34](=[O:36])[CH2:35][C@:23]2(/[CH:40]=[CH:41]/[C:42](=[O:52])[NH:43][C@@H:44]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=3)[CH3:45])[CH2:22][CH2:21][C@:20]3([CH3:53])[C@H:25]([CH2:26][CH2:27][C@H:28]4[C@@:19]3([CH3:54])[CH2:18][CH2:17][C@@H:16]3[C@:29]4([CH3:32])[CH2:30][CH2:31][C@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:1])([CH3:57])[C:3]([OH:5])=[O:4])[C:15]3([CH3:55])[CH3:56])[C:24]=12)([CH3:38])[CH3:39].[F:61][C:60]([F:63])([F:62])[C:58]([OH:64])=[O:59]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117701653HCID 117701653, compound

Product 2

HCID 6422Trifluoroacetic acidYield 44.6%HCID 71611023HCID 71611023, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butyl 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3a-((E)-3-oxo-3-(((R)-1-(pyridin-2-yl)ethyl)amino)prop-1-en-1-yl)-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 (470 mg, 0.599 mmol) in dichloromethane (10 mL) stirred at rt was added TFA (5 mL). The reaction mixture was stirred at rt for 2 h. Then, it was evaporated in vacuo to get crude product. This material was purified by preparative-HPLC to provide the title compound trifluoroacetic acid salt (225 mg, 0.267 mmol, 44.6%) as a light yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ=9.23 (d, J=6.8 Hz, 1H), 8.75 (d, J=3.5 Hz, 1H), 8.32 (t, J=7.7 Hz, 1H), 7.92 (d, J=7.8 Hz, 1H), 7.84-7.69 (m, 1H), 6.77 (d, J=15.8 Hz, 1H), 5.89 (d, J=15.8 Hz, 1H), 5.49-5.21 (m, 1H), 4.50 (dd, J=5.4, 10.7 Hz, 1H), 3.32-3.05 (m, 1H), 2.78-2.49 (m, 3H), 2.33-2.01 (m, 3H), 2.03-0.63 (m, 47H); LC/MS: m/z calculated 728.5. Found 729.4 (M+1)+.

Workup

  1. customThen, it was evaporated in vacuo
  2. customto get crude product
  3. customThis material was purified by preparative-HPLC

Sources & evidence

ORD record
ord-4a12d9a48648434bade03b4c1942a5f4
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

Loading…