Trifluoroacetic acid → HCID 71610786, compound

HRID 524449Notes

Reaction equation

HRID 524449 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][C:50]([Cl:53])=[CH:49][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:50]1[CH:49]=[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]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117701658HCID 117701658, compound

Product 1

HCID 71610786HCID 71610786, compoundYield 72.7%

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-(((R)-1-(4-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 (2.5 g, 3.05 mmol) in Dichloromethane (20 mL) was added TFA (13 mL, 3.05 mmol). The reaction mixture was stirred at r.t. for 2 hs and evaporated in vacuo to afford crude product, which was diluted with DCM, washed with water, saturated NaHCO3 twice, water, 2 M HCl, water, and the organic layer was concentrated, diluted with MeOH/H2O (1:5, 36 mL) and freeze-dried under high vacuo to give the product 4-(((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-(((R)-1-(4-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)oxy)-2,2-dimethyl-4-oxobutanoic acid (1.7 g, 2.217 mmol, 72.6%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) d=12.34-12.04 (m, 1H), 8.43 (d, J=7.8 Hz, 1H), 7.53-7.18 (m, 4H), 6.63 (d, J=15.8 Hz, 1H), 5.92 (d, J=15.8 Hz, 1H), 4.94 (quin, J=7.0 Hz, 1H), 4.39 (dd, J=4.6, 10.9 Hz, 1H), 3.18 (dt, J=6.7, 13.7 Hz, 1H), 2.70 (dd, J=4.3, 10.5 Hz, 2H), 2.58-2.52 (m, 1H), 2.34-1.99 (m, 3H), 1.99-0.56 (m, 48H); LC/MS: m/z calculated 761.4. Found 762.3 (M+1)+.

Workup

  1. customevaporated in vacuo
  2. customto afford crude product, which
  3. washwashed with water, saturated NaHCO3 twice
  4. concentrationwater, 2 M HCl, water, and the organic layer was concentrated
  5. additiondiluted with MeOH/H2O (1:5, 36 mL)
  6. customfreeze-dried under high vacuo

Sources & evidence

ORD record
ord-6a4a436701114820939cc025a289eb7c
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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