Acetonitrile → HCID 86575233, compound

HRID 524448Notes

Reaction equation

HRID 524448 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]([Cl: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:57]([OH:63])([C:59]([F:62])([F:61])[F:60])=[O:58].CC#N>ClCCl>[C:57]([OH:63])([C:59]([F:62])([F:61])[F:60])=[O:58].[OH2:4].[Cl: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

6

Reactant 3

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 117701494HCID 117701494, compound

Product 2

HCID 22392675Trifluoroacetic acid waterYield 0.05%HCID 86575233HCID 86575233, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butyl 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-((4-chlorophenyl)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 (230 mg, 0.291 mmol) in Dichloromethane (DCM) (4 mL) was added TFA (2 mL, 0.291 mmol). The reaction mixture was stirred at r.t for 2 hs and evaporated in vacuo to afford crude product, which was purified by preparative-HPLC (Mobile Phase: A=0.05% TFA/H2O, B=MeCN) to give the product 4-(((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-((4-chlorophenyl)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 (100 mg, 0.136 mmol, 46.8%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.60-7.53 (m, 3H), 7.28 (d, J=8.4 Hz, 2H), 7.12 (d, J=15.6 Hz, 1H), 5.84 (d, J=15.6 Hz, 1H), 4.50 (dd, J=11.2, 5.2 Hz, 1H), 3.22 (m, 1H), 2.77 (d, J=11.6 Hz, 1H), 2.68 (d, J=16.0 Hz, 1H), 2.57 (d, J=15.6 Hz, 1H), 2.32 (d, J=18.8 Hz, 1H), 2.20 (d, J=19.2 Hz, 1H), 2.11 (d, J=12.0 Hz, 1H), 1.93-0.77 (m, 44H); LC/MS: m/z calculated 733.4. Found 734.3 (M+1)+.

Workup

  1. customevaporated in vacuo
  2. customto afford crude product, which
  3. customwas purified by preparative-HPLC (Mobile Phase

Sources & evidence

ORD record
ord-13e798807a754821857014ac0063c463
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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