Trifluoroacetic acid → HCID 71596749, compound

HRID 405059Notes

Reaction equation

HRID 405059 reaction equation
[CH3:1][C@:2]12[C@@:19]3([CH3:20])[C@@H:10]([C@:11]4([CH3:36])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:22])([CH3:21])[C:14]([C:23]3[CH:35]=[CH:34][C:26]([C:27]([O:29]C(C)(C)C)=[O:28])=[CH:25][CH:24]=3)=[CH:13][CH2:12]4)[CH2:9][CH2:8][C@@H:7]1[C@H:6]1[C@H:37]([C:40]([CH3:42])=[CH2:41])[CH2:38][CH2:39][C@:5]1([CH2:43][NH:44][CH2:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=1)[CH2:4][CH2:3]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C@:2]12[C@@:19]3([CH3:20])[C@@H:10]([C@:11]4([CH3:36])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:21])([CH3:22])[C:14]([C:23]3[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:34][CH:35]=3)=[CH:13][CH2:12]4)[CH2:9][CH2:8][C@@H:7]1[C@H:6]1[C@H:37]([C:40]([CH3:42])=[CH2:41])[CH2:38][CH2:39][C@:5]1([CH2:43][NH:44][CH2:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=1)[CH2:4][CH2:3]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86676403tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-((2-(pyridin-2-yl)ethylamino)methyl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Product 1

HCID 71596749HCID 71596749, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-((2-(pyridin-2-yl)ethylamino)methyl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (0.119 g, 0.127 mmol) in DCM (1 ml) was added TFA (0.4 ml, 5.19 mmol). The mixture was stirred at rt for 3.5 h and the mixture was concentrated under reduced pressure. The residue was purified by prep. HPLC. The fractions containing the expected product were combined and concentrated under reduced pressure to give the title compound as a light-yellow foam (61 mg, 0.094 mmol, 74.3% yield). LCMS: m/e 647.4 (M−H)−, 2.20 min (method 6). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.42-8.48 (m, 1H),7.95 (d, J=8.28 Hz, 2H), 7.65 (td, J=7.65, 1.76 Hz, 1H), 7.17-7.24 (m, 2H), 7.14 (d, J=8.03 Hz, 2H), 5.29 (d, J=4.52 Hz, 1H), 4.71 (br. s., 1H), 4.61 (br. s., 1H), 3.45-3.59 (m, 2H), 3.18-3.32 (m, 3H), 2.74 (d, J=12.30 Hz, 1H), 2.45 (br. s., 1H), 1.70 (s, 3H), 1.05 (s, 3H), 1.01 (s, 3H), 0.98-2.13 (m, 24H), 0.96 (s, 3H), 0.94 (br. s., 3H), 0.92 (br. s., 3H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was purified by prep
  3. additionThe fractions containing the expected product
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6da5578fd0c44f25a25d9797422cad4d
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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