Acetonitrile → HCID 86575074, compound

HRID 524460Notes

Reaction equation

HRID 524460 reaction equation
[CH3:1][C:2]([CH3:59])([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([CH3:56])[C@@H:28]2[CH2:27][CH2:26][C@H:25]2[C@@:20]3([CH3:55])[CH2:21][CH2:22][C@@:23]3(/[CH:40]=[CH:41]/[C:42]([NH:44][C:45]4([C:48]5[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=5[Cl:54])[CH2:47][CH2:46]4)=[O:43])[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]32)[C:15]1([CH3:58])[CH3:57])=[O:12])[C:3]([O:5]C(C)(C)C)=[O:4].[C:60]([OH:66])([C:62]([F:65])([F:64])[F:63])=[O:61].CC#N>ClCCl>[C:60]([OH:66])([C:62]([F:65])([F:64])[F:63])=[O:61].[OH2:4].[Cl:54][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=1[C:45]1([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]([CH3:55])([CH2:21][CH2:22]3)[C@@:19]3([CH3:56])[C@@H:28]([C@:29]4([CH3:32])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:58])([CH3:57])[C@@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:1])([CH3:59])[C:3]([OH:5])=[O:4])[CH2:31][CH2:30]4)[CH2:27][CH2:26]2)[CH2:47][CH2:46]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 117701662HCID 117701662, compound

Product 2

HCID 22392675Trifluoroacetic acid waterYield 0.05%HCID 86575074HCID 86575074, compoundYield 78.7%

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-((1-(2-chlorophenyl)cyclopropyl)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 (300 mg, 0.361 mmol) in dichloromethane (6 mL) was added TFA (3 mL, 0.361 mmol). The reaction mixture was stirred at rt for 2 hr 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 title compound (110 mg, 0.142 mmol, 39.3%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=12.23 (br. s., 1H), 8.67 (d, J=7.3 Hz, 1H), 7.67 (br. s., 1H), 7.52-7.13 (m, 3H), 6.69-6.41 (m, 1H), 6.00-5.76 (m, 1H), 4.49-4.20 (m, 1H), 3.29-3.02 (m, 1H), 2.78-2.60 (m, 1H), 2.30-0.57 (m, 53H); LC/MS: m/z calculated 773.4. Found 774.4 (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-3469475331ec4dcb94876b4d757a9a1b
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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