Trifluoroacetic acid → HCID 71611454, compound

HRID 524473Notes

Reaction equation

HRID 524473 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[CH:53]=[CH:52][CH:51]=[C:50]([Cl:54])[CH: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:50]1[CH:49]=[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)[CH:53]=[CH:52][CH:51]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 18373917Acetonitrile--water (1/1)HCID 117701556HCID 117701556, compound

Product 1

HCID 71611454HCID 71611454, compoundYield 49.7%

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-(3-chlorophenyl)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 (280 mg, 0.332 mmol) in DCM (6 mL) was added TFA (3 mL, 0.332 mmol). The reaction mixture was stirred at rt for 2 hr and evaporated in vacuo to afford crude product. This was diluted with DCM (30 mL), and washed with water, saturated NaHCO3, water, saturated NH4CI and then 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 (130 mg, 48%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=12.16 (br. s., 1H), 8.62 (s, 1H), 7.34-7.17 (m, 2H), 7.14 (s, 1H), 7.05 (d, J=7.5 Hz, 1H), 6.57 (s, 1H), 4.40 (dd, J=4.4, 10.9 Hz, 1H), 3.23-3.08 (m, 1H), 2.83-0.62 (m, 57H); LC/MS: m/z calculated 787.5. Found 788.2 (M+1)+.

Workup

  1. customevaporated in vacuo
  2. customto afford crude product
  3. washwashed with water, saturated NaHCO3, water, saturated NH4CI
  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-7fc3937560fd44cca1299ccd6826d928
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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