Trifluoroacetic acid → HCID 86575001, compound

HRID 524457Notes

Reaction equation

HRID 524457 reaction equation
[CH3:1][C:2]([CH3:56])([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([CH3:53])[C@@H:28]2[CH2:27][CH2:26][C@H:25]2[C@@:20]3([CH3:52])[CH2:21][CH2:22][C@@:23]3(/[CH:40]=[CH:41]/[C:42]([NH:44][C:45]4[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=4)=[O:43])[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]32)[C:15]1([CH3:55])[CH3:54])=[O:12])[C:3]([O:5]C(C)(C)C)=[O:4].C(O)(C(F)(F)F)=O.CCCCCC>ClCCl>[F:51][C:48]1[CH:49]=[CH:50][C:45]([NH:44][C:42](=[O:43])/[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]([CH3:52])([CH2:21][CH2:22]3)[C@@:19]3([CH3:53])[C@@H:28]([C@:29]4([CH3:32])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:54])([CH3:55])[C@@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:1])([CH3:56])[C:3]([OH:5])=[O:4])[CH2:31][CH2:30]4)[CH2:27][CH2:26]2)=[CH:46][CH:47]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8058HexaneHCID 117701505HCID 117701505, compound

Product 1

HCID 86575001HCID 86575001, compoundYield 69%

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-((4-fluorophenyl)amino)-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, 0.323 mmol), TFA (1 mL, 12.98 mmol) in dichloromethane (4 mL) stirred at rt. The reaction mixture was stirred at rt for 2 h, washed with saturated NaHCO3 in water (300 mL×8); followed by 2 M HCl (300 mL), water, and then brine. The organic layer was dried over Na2SO4, filtered and concentrated to give the crude product, which was solved into DCM (80 mL) and hexane (120 mL) was added. The suspension was filtered, washed with hexane to afford the crude product, and then purified by preparative-HPLC to afford the title compound (160 mg, 68%) as a light white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.56 (br. s., 3H), 7.23-6.93 (m, 3H), 5.96-5.75 (m, 1H), 4.52 (dd, J=5.1, 10.9 Hz, 1H), 3.33-3.13 (m, 1H), 2.88-2.51 (m, 3H), 2.45-0.72 (m, 47H); LC/MS: m/z calculated 717.4. Found 718.3 (M+1)+.

Workup

  1. washwashed with saturated NaHCO3 in water (300 mL×8)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. additionwas added
  7. filtrationThe suspension was filtered
  8. washwashed with hexane
  9. customto afford the crude product
  10. custompurified by preparative-HPLC

Sources & evidence

ORD record
ord-cb2f7ec7dab54cca8e614d1480e317a5
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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