Hydrochloric Acid → 4-{3-[2-(3-Bromobenzoylamino)ethoxy]-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl}pentanoic acid

HRID 1280870Notes

Reaction equation

HRID 1280870 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:40]=[CH:41][CH:42]=1)[C:5]([NH:7][CH2:8][CH2:9][O:10][CH:11]1[CH2:27][CH:26]2[C:14]([CH3:39])([CH:15]3[CH:23]([CH:24]([OH:28])[CH2:25]2)[CH:22]2[C:18]([CH3:37])([CH:19]([CH:29]([CH3:36])[CH2:30][CH2:31][C:32]([O:34]C)=[O:33])[CH2:20][CH2:21]2)[CH:17]([OH:38])[CH2:16]3)[CH2:13][CH2:12]1)=[O:6].[OH-].[Na+].Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:40]=[CH:41][CH:42]=1)[C:5]([NH:7][CH2:8][CH2:9][O:10][CH:11]1[CH2:27][CH:26]2[C:14]([CH3:39])([CH:15]3[CH:23]([CH:24]([OH:28])[CH2:25]2)[CH:22]2[C:18]([CH3:37])([CH:19]([CH:29]([CH3:36])[CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH2:20][CH2:21]2)[CH:17]([OH:38])[CH2:16]3)[CH2:13][CH2:12]1)=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18425126Methyl 4-{3-[2-(3-bromobenzoylamino)ethoxy]-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl}pentanoate

Product 1

HCID 184251284-{3-[2-(3-Bromobenzoylamino)ethoxy]-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl}pentanoic acidYield 93.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

600 mg of methyl 4-{3-[2-(3-bromobenzoylamino)ethoxy]-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl}pentanoate are dissolved in 19 ml of methanol and 4.6 ml of a 1N aqueous NaOH solution are added. The mixture is stirred at RT for 6 hours, then poured into 150 ml of a 2N aqueous HCl solution and extracted 4 times using 150 ml of MTB each time. The extract is dried over Na2SO4 and the solvent is removed in vacuo. 550 mg of a viscous oil are obtained, which are employed further as such.

Workup

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

Sources & evidence

ORD record
ord-71eec1ada0954e84834435dd77eb2580
Source dataset
uspto-grants-2002_09
Patent number
US06451781B1

Reaction notes

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