Trifluoroacetic acid → HCID 68357928, compound

HRID 85688

Reaction equation

HRID 85688 reaction equation
[CH3:1][C@:2]12[C@@:19]3([CH3:20])[C@@H:10]([C@:11]4([CH3:33])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:22])([CH3:21])[C:14]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29]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:34]([C:37]([CH3:39])=[CH2:38])[CH2:35][CH2:36][C@:5]1([NH:40][CH2:41][CH2:42][NH:43][C:44]1[N:45]=[N:46][CH:47]=[CH:48][CH:49]=1)[CH2:4][CH2:3]2.O.[OH-].[Li+].C1COCC1.C(O)(C(F)(F)F)=O>O.CO>[CH3:1][C@:2]12[C@@:19]3([CH3:20])[C@@H:10]([C@:11]4([CH3:33])[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:31][CH:32]=3)=[CH:13][CH2:12]4)[CH2:9][CH2:8][C@@H:7]1[C@H:6]1[C@H:34]([C:37]([CH3:39])=[CH2:38])[CH2:35][CH2:36][C@:5]1([NH:40][CH2:41][CH2:42][NH:43][C:44]1[N:45]=[N:46][CH:47]=[CH:48][CH:49]=1)[CH2:4][CH2:3]2

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68358211methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-(2-(pyridazin-3-ylamino)ethylamino)-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 68357928HCID 68357928, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-(2-(pyridazin-3-ylamino)ethylamino)-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 and lithium hydroxide monohydrate (2.3 mg, 0.055 mmol) in a mixture of water (0.5 mL), THF (0.25 mL) and MeOH (0.25 mL) was stirred at rt for 2.5 days. Purification of the crude mixture by reverse phase preparative HPLC using Prep HPLC Method 10 gave the title compound as a white solid (5.0 mg, 100% yield) bis TFA salt. LCMS: m/e 651.5 (M+H)+, 2.26 min (method 11).

Workup

  1. customPurification of the crude mixture by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-7b97503e723e415ebc5dc7c9bf5a6e36
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Linked notes

Loading…