Acetonitrile → Trifluoroacetic acid

HRID 524451Notes

Reaction equation

HRID 524451 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](=[O:53])[NH:43][C:44]4([C:47]5[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=5)[CH2:46][CH2:45]4)[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:59]([OH:65])([C:61]([F:64])([F:63])[F:62])=[O:60].CC#N>ClCCl>[C:59]([OH:65])([C:61]([F:64])([F:63])[F:62])=[O:60].[OH2:4].[CH:37]([C:33]1[C:34](=[O:36])[CH2:35][C@:23]2(/[CH:40]=[CH:41]/[C:42](=[O:53])[NH:43][C:44]3([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=4)[CH2:46][CH2:45]3)[CH2:22][CH2:21][C@:20]3([CH3:54])[C@H:25]([CH2:26][CH2:27][C@H:28]4[C@@:19]3([CH3:55])[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])([CH3:58])[C:3]([OH:5])=[O:4])[C:15]3([CH3:56])[CH3:57])[C:24]=12)([CH3:39])[CH3:38].[F:62][C:61]([F:64])([F:63])[C:59]([OH:65])=[O:60]

Participants

7

Reactant 3

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 89619146HCID 89619146, compound

Product 3

HCID 6422Trifluoroacetic acidYield 11.4%HCID 22392675Trifluoroacetic acid waterYield 0.05%HCID 71610907HCID 71610907, 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-((1-(pyridin-2-yl)cyclopropyl)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 (460 mg, 0.577 mmol) in dichloromethane (6 mL) was added TFA (3 mL, 0.577 mmol). The reaction mixture was stirred at r.t for 2 hr and evaporated in vacuo to afford crude product, which was purified by preparative-HPLC (Mobile Phase: A=0.05% TFA/H2O, B=MeCN) to give the title compound, trifluoroacetic acid salt (30 mg, 0.033 mmol, 5.78%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=12.16 (br. s., 1H), 8.80 (s, 1H), 8.42 (d, J=4.0 Hz, 1H), 7.66 (t, J=7.4 Hz, 1H), 7.29-7.06 (m, 2H), 6.69 (d, J=15.8 Hz, 1H), 5.97 (d, J=15.8 Hz, 1H), 4.40 (dd, J=4.6, 10.9 Hz, 1H), 3.27-3.13 (m, 1H), 3.02-2.87 (m, 1H), 2.80 (d, J=11.5 Hz, 1H), 2.59-2.52 (m, 1H), 2.30-0.73 (m, 51H); LC/MS: m/z calculated 740.5. Found 741.3 (M+1)+.

Workup

  1. customevaporated in vacuo
  2. customto afford crude product, which
  3. customwas purified by preparative-HPLC (Mobile Phase

Sources & evidence

ORD record
ord-47877c4b85f342c1a27923d0992e62df
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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