Hydroxyphenylacetic acid → Methyl 4-(7,12-dihydroxy-3-{2-[2-(4-hydroxyphenyl)acetylamino]ethoxy}-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl)pentanoate

HRID 1280866Notes

Reaction equation

HRID 1280866 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:21][CH:20]2[C:8]([CH3:33])([CH:9]3[CH:17]([CH:18]([OH:22])[CH2:19]2)[CH:16]2[C:12]([CH3:31])([CH:13]([CH:23]([CH3:30])[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:14][CH2:15]2)[CH:11]([OH:32])[CH2:10]3)[CH2:7][CH2:6]1.[OH:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][C:42](O)=[O:43])=[CH:37][CH:36]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[OH:22][CH:18]1[CH:17]2[CH:9]([CH2:10][CH:11]([OH:32])[C:12]3([CH3:31])[CH:16]2[CH2:15][CH2:14][CH:13]3[CH:23]([CH3:30])[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:8]2([CH3:33])[CH:20]([CH2:21][CH:5]([O:4][CH2:3][CH2:2][NH:1][C:42](=[O:43])[CH2:41][C:38]3[CH:39]=[CH:40][C:35]([OH:34])=[CH:36][CH:37]=3)[CH2:6][CH2:7]2)[CH2:19]1

Participants

6

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 18425132Methyl 4-[3-(2-aminoethoxy)-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl]pentanoate

Product 1

HCID 69725262Methyl 4-(7,12-dihydroxy-3-{2-[2-(4-hydroxyphenyl)acetylamino]ethoxy}-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl)pentanoateYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

700 mg of methyl 4-[3-(2-aminoethoxy)-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl]pentanoate, 230 mg of 4-hydroxyphenylacetic acid and 305 mg of HOBT are dissolved in 10 ml of THF and a solution of 342 mg of DCC in 10 ml of THF is injected at 0° C. The mixture is stirred at 0° C. for one hour and then at RT for 25 hours. The precipitate is filtered off, the filtrate is diluted with 150 ml of a 10% aqueous NaHCO3 solution and the mixture is extracted three times with 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 660 mg of a colorless oil.

Workup

  1. customis injected at 0° C
  2. waitat RT for 25 hours
  3. filtrationThe precipitate is filtered off
  4. additionthe filtrate is diluted with 150 ml of a 10% aqueous NaHCO3 solution
  5. extractionthe mixture is extracted three times with 100 ml of EA each time
  6. dry with materialThe extract is dried over Na2SO4
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-a459cc98f0a942af8e6ca85bb0301380
Source dataset
uspto-grants-2002_09
Patent number
US06451781B1

Reaction notes

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