Acetonitrile → Trifluoroacetic acid

HRID 524459Notes

Reaction equation

HRID 524459 reaction equation
[CH3:1][C:2]([CH3:55])([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([CH3:52])[C@@H:28]2[CH2:27][CH2:26][C@H:25]2[C@@:20]3([CH3:51])[CH2:21][CH2:22][C@@:23]3(/[CH:40]=[CH:41]/[C:42](=[O:50])[NH:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=4)[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]32)[C:15]1([CH3:54])[CH3:53])=[O:12])[C:3]([O:5]C(C)(C)C)=[O:4].[C:56]([OH:62])([C:58]([F:61])([F:60])[F:59])=[O:57].CC#N.[Cl:66]CCl>>[C:56]([OH:62])([C:58]([F:61])([F:60])[F:59])=[O:57].[OH2:4].[Cl:66][C:47]1[CH:48]=[CH:49][C:44]([NH:43][C:42](=[O:50])/[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]([CH3:51])([CH2:21][CH2:22]3)[C@@:19]3([CH3:52])[C@@H:28]([C@:29]4([CH3:32])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:54])([CH3:53])[C@@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:55])([CH3:1])[C:3]([OH:5])=[O:4])[CH2:31][CH2:30]4)[CH2:27][CH2:26]2)=[N:45][CH:46]=1.[F:59][C:58]([F:61])([F:60])[C:56]([OH:62])=[O:57]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 117701589HCID 117701589, compound

Product 3

HCID 6422Trifluoroacetic acidYield 30%HCID 22392675Trifluoroacetic acid waterYield 0.05%HCID 89641077HCID 89641077, compound

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-(pyridin-2-ylamino)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 (300 mg, 0.396 mmol) in dichloromethane (6 mL) was added TFA (3 mL, 0.396 mmol). The reaction mixture was stirred at rt 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 (100 mg, 0.119 mmol, 30.0%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=10.72 (br. s., 1H), 8.33 (br. s., 1H), 8.14 (br. s., 1H), 7.83 (br. s., 1H), 7.33-6.97 (m, 1H), 6.97-6.75 (m, 1H), 6.41-6.13 (m, 1H), 4.52-4.25 (m, 1H), 3.35-3.06 (m, 1H), 2.98-2.65 (m, 2H), 2.35-0.53 (m, 47H); LC/MS: m/z calculated 700.5. Found 701.3 (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-e04fea7fefea466988141bfff2397832
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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