Hydrochloric Acid → Ethyl 3-{4-[4-({2-[17-(3-Carboxy-1-methylpropyl)-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-3-yloxy]ethylcarbamoyl}methyl)phenoxy]-3,5-difluorophenyl}-2-methylacrylate

HRID 1280868Notes

Reaction equation

HRID 1280868 reaction equation
[OH:1][CH:2]1[CH:18]2[CH:10]([CH2:11][CH:12]([OH:27])[C:13]3([CH3:26])[CH:17]2[CH2:16][CH2:15][CH:14]3[CH:19]([CH3:25])[CH2:20][CH2:21][C:22]([OH:24])=[O:23])[C:9]2([CH3:28])[CH:4]([CH2:5][CH:6]([O:29][CH2:30][CH2:31][NH:32][C:33](=[O:42])[CH2:34][C:35]3[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=3)[CH2:7][CH2:8]2)[CH2:3]1.[CH3:43][C:44](=[CH:50][C:51]1[CH:56]=[C:55]([F:57])[C:54](F)=[C:53]([F:59])[CH:52]=1)[C:45]([O:47][CH2:48][CH3:49])=[O:46].C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[C:22]([CH2:21][CH2:20][CH:19]([CH:14]1[C:13]2([CH3:26])[CH:17]([CH:18]3[CH:10]([CH2:11][CH:12]2[OH:27])[C:9]2([CH3:28])[CH:4]([CH2:5][CH:6]([O:29][CH2:30][CH2:31][NH:32][C:33]([CH2:34][C:35]4[CH:36]=[CH:37][C:38]([O:41][C:54]5[C:53]([F:59])=[CH:52][C:51]([CH:50]=[C:44]([CH3:43])[C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:56][C:55]=5[F:57])=[CH:39][CH:40]=4)=[O:42])[CH2:7][CH2:8]2)[CH2:3][CH:2]3[OH:1])[CH2:16][CH2:15]1)[CH3:25])([OH:24])=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 53919072Ethyl 2-methyl-3-(3,4,5-trifluorophenyl)acrylateHCID 69725368HCID 69725368, compound

Product 1

HCID 69726546Ethyl 3-{4-[4-({2-[17-(3-Carboxy-1-methylpropyl)-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-3-yloxy]ethylcarbamoyl}methyl)phenoxy]-3,5-difluorophenyl}-2-methylacrylateYield 62.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

610 mg of 4-(7,12-dihydroxy-3-{2-[2-(4-hydroxyphenyl)acetylamino]ethoxy}-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl)pentanoic acid, 232 mg of ethyl 2-methyl-3-(3,4,5-trifluorophenyl)acrylate and 393 mg of K2CO3 are suspended in 5 ml of DMF (anhydrous) and the suspension is stirred at 150° C. for 160 minutes. After cooling, the reaction mixture is taken up using 150 ml of a 2N aqueous HCl solution and extracted three times using 100 ml of EA each time. The extract is dried over Na2SO4 and the solvent is removed in vacuo. Chromatography on silica gel using EA/MeOH 10:1 yields 480 mg of resinous product.

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times
  3. dry with materialThe extract is dried over Na2SO4
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-d4b9aa4c49c34960b313b89001e25691
Source dataset
uspto-grants-2002_09
Patent number
US06451781B1

Reaction notes

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