(4s,5r)-1-{(2r,9e)-11-[3,17beta-Bis(benzyloxy)estra-1,3,5(10),9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoyl}-3,4-dimethyl-5-phenylimidazolidin-2-one → (4S, 5R)-1-{(2R)-11-[3,17beta-Dihydroxyestra-1,3,5(10)-trien-11beta-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-undecanoyl}-3,4-dimethyl-5-phenylimidazolidin-2-one

HRID 1582837Notes

Reaction equation

HRID 1582837 reaction equation
C([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][C:22]=3[CH2:27]/[CH:28]=[CH:29]/[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C@H:36]([CH2:53][CH2:54][C:55]([F:67])([F:66])[C:56]([F:65])([F:64])[C:57]([F:63])([F:62])[C:58]([F:61])([F:60])[F:59])[C:37]([N:39]3[C@H:43]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[C@H:42]([CH3:50])[N:41]([CH3:51])[C:40]3=[O:52])=[O:38])([CH3:20])[C@@H:18]([O:68]CC3C=CC=CC=3)[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)C1C=CC=CC=1.C(OC1C=CC2C3[C@H]([C@H]4[C@@](CC=3C/C=C\CCCCCC[C@H](CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(N3[C@H](C5C=CC=CC=5)[C@H](C)N(C)C3=O)=O)(C)[C@@H](OCC3C=CC=CC=3)CC4)CCC=2C=1)C1C=CC=CC=1>CO.O1CCCC1.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][C@@H:22]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C@H:36]([CH2:53][CH2:54][C:55]([F:67])([F:66])[C:56]([F:64])([F:65])[C:57]([F:62])([F:63])[C:58]([F:59])([F:60])[F:61])[C:37]([N:39]3[C@H:43]([C:44]5[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=5)[C@H:42]([CH3:50])[N:41]([CH3:51])[C:40]3=[O:52])=[O:38])([CH3:20])[C@@H:18]([OH:68])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1

Participants

6

Reactant 2

HCID 86588541(4s,5r)-1-{(2r,9e)-11-[3,17beta-Bis(benzyloxy)estra-1,3,5(10),9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoyl}-3,4-dimethyl-5-phenylimidazolidin-2-oneHCID 86588542(4S,5R)-1-[(2R,9Z)-11-[3,17beta-bis(benzyloxy)estra-1,3,5(10),9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoyl}-3,4-dimethyl-5-phenylimidazolidin-2-one

Product 1

HCID 86588540(4S, 5R)-1-{(2R)-11-[3,17beta-Dihydroxyestra-1,3,5(10)-trien-11beta-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-undecanoyl}-3,4-dimethyl-5-phenylimidazolidin-2-oneYield 70%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The mixture of (4S, 5R)-1-{(2R, 9E)-11-[3,17β-bis-(benzyloxy)estra-1,3,5(10), 9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoyl}-3,4-dimethyl-5-phenylimidazolidin-2-one and (4S, 5R)-1-{(2R, 9Z)-11-[3,17β-bis(benzyloxy)estra-1,3,5(10), 9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoyl}-3,4-dimethyl-5-phenylimidazolidin-2-one (283 mg, 0.27 mmol) was dissolved in a mixed solvent of methanol (12 ml) and tetrahydrofuran (1.2 ml), followed by addition of palladium hydroxide/carbon (85 mg) at room temperature. After purging with hydrogen, the reaction mixture was stirred for 1 day at room temperature. After the reaction mixture was filtered, the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=3/7) to give (4S, 5R)-1-{(2R)-11-[3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoyl}-3,4-dimethyl-5-phenylimidazolidin-2-one (164 mg, Yield 70%).

Workup

  1. customAfter purging with hydrogen
  2. filtrationAfter the reaction mixture was filtered
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=3/7)

Sources & evidence

ORD record
ord-ee4f554572f74093899af163151e00d1
Source dataset
uspto-grants-2004_05
Patent number
US06737417B2

Reaction notes

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