Trifluoroacetic acid → HCID 71611311, compound

HRID 524472Notes

Reaction equation

HRID 524472 reaction equation
[CH3:1][C:2]([CH3:60])([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([CH3:57])[C@@H:28]2[CH2:27][CH2:26][C@H:25]2[C@@:20]3([CH3:56])[CH2:21][CH2:22][C@@:23]3(/[CH:40]=[C:41](\[CH3:55])/[C:42]([NH:44][C:45]4([C:48]5[N:53]=[CH:52][C:51]([Cl:54])=[CH:50][N: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([CH3:59])[CH3:58])=[O:12])[C:3]([O:5]C(C)(C)C)=[O:4].C(O)(C(F)(F)F)=O.CC#N.O>C(Cl)Cl>[Cl:54][C:51]1[CH:52]=[N:53][C:48]([C:45]2([NH:44][C:42](=[O:43])/[C:41](/[CH3:55])=[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]([CH3:56])([CH2:21][CH2:22]4)[C@@:19]4([CH3:57])[C@@H:28]([C@:29]5([CH3:32])[C@@H:16]([CH2:17][CH2:18]4)[C:15]([CH3:58])([CH3:59])[C@@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:1])([CH3:60])[C:3]([OH:5])=[O:4])[CH2:31][CH2:30]5)[CH2:27][CH2:26]3)[CH2:47][CH2:46]2)=[N:49][CH:50]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 18373917Acetonitrile--water (1/1)HCID 117701702HCID 117701702, compound

Product 1

HCID 71611311HCID 71611311, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-tert-butyl 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-((1-(5-chloropyrimidin-2-yl)cyclopropyl)amino)-2-methyl-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 (250 mg, 0.295 mmol) in DCM (6 mL) was added TFA (3 mL, 0.295 mmol). The reaction mixture was stirred at rt for 2 hr and evaporated in vacuo to afford crude product. This material was diluted with DCM (30 mL), and washed with water, saturated NaHCO3, water, saturated NH4CI and water. The organic layer was dried over Na2SO4, filtered and concentrated to obtain a residue which was dissolved into MeCN—H2O (1:2, 9 mL) and freeze-dried to give the title compound (120 mg, 0.149 mmol, 50.4%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=12.22 (br. s., 1H), 8.75 (s, 2H), 8.60 (s, 1H), 6.57 (s, 1H), 4.39 (dd, J=4.8, 11.3 Hz, 1H), 3.24-3.10 (m, 1H), 2.82-0.59 (m, 57H); LC/MS: m/z calculated 789.5. Found 790.3 (M+1)+.

Workup

  1. customevaporated in vacuo
  2. customto afford crude product
  3. washwashed with water, saturated NaHCO3, water, saturated NH4CI and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain a residue which
  8. customfreeze-dried

Sources & evidence

ORD record
ord-7ad5ce57e74c4aacba070f074d87a174
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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