Trifluoroacetic acid → HCID 71611167, compound

HRID 524463Notes

Reaction equation

HRID 524463 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]([NH:44][C@H:45]([C:47]4[CH:52]=[CH:51][CH:50]=[C:49]([Cl:53])[CH:48]=4)[CH3:46])=[O:43])[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(O)(C(F)(F)F)=O>ClCCl>[Cl:53][C:49]1[CH:48]=[C:47]([C@@H:45]([NH:44][C:42](=[O:43])/[CH:41]=[CH:40]/[C@:23]23[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]2[C@@H:25]2[C@@:20]([CH3:54])([CH2:21][CH2:22]3)[C@@:19]3([CH3:55])[C@@H:28]([C@:29]4([CH3:32])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:56])([CH3:57])[C@@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:1])([CH3:58])[C:3]([OH:5])=[O:4])[CH2:31][CH2:30]4)[CH2:27][CH2:26]2)[CH3:46])[CH:52]=[CH:51][CH:50]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117701522HCID 117701522, compound

Product 1

HCID 71611167HCID 71611167, compoundYield 88%

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-(((S)-1-(3-chlorophenyl)ethyl)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 (12 g, 14.66 mmol) in dichloromethane (130 mL) was added TFA (80 mL, 14.66 mmol). The reaction mixture was stirred at rt for 2 hr and diluted with DCM, washed with water twice. And the organic layer was concentrated, diluted with MeCN/H2O (1:5, 36 mL) and freeze-dried under high vacuo to give the title compound (9.9 g, 12.89 mmol, 88%). This material was combined with several batches made under similar conditions and freeze dried together for characterization (31 g, 41 mmol) as a light yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.38-7.13 (m, 4H), 6.97 (d, J=15.6 Hz, 1H), 5.82-5.59 (m, 2H), 5.26-5.06 (m, 1H), 4.50 (dd, J=5.3, 11.0 Hz, 1H), 3.29-3.09 (m, 1H), 2.81-2.48 (m, 3H), 2.37-2.00 (m, 3H), 2.00-0.68 (m, 47H).

Workup

  1. washwashed with water twice
  2. concentrationAnd the organic layer was concentrated
  3. additiondiluted with MeCN/H2O (1:5, 36 mL)
  4. customfreeze-dried under high vacuo

Sources & evidence

ORD record
ord-829baa80b57e4844b69a18dd36b69ee2
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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