(4S,5R)-3,4-dimethyl-1-[(2R,9E)-11-(17beta-hydroxy-3-methoxyestra-1,3,5(10)-trien-7alpha-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoyl]-5-phenylimidazolidin-2-one → (4S,5R)-3,4-dimethyl-1-[(2R)-11-(17beta-hydroxy-3-methoxyestra-1,3,5(10)-trien-7alpha-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoyl]-5-phenylimidazolidin-2-one

HRID 460486Notes

Reaction equation

HRID 460486 reaction equation
[CH3:1][N:2]1[C@@H:6]([CH3:7])[C@@H:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]([C:14](=[O:61])[C@@H:15]([CH2:46][CH2:47][C:48]([F:60])([F:59])[C:49]([F:58])([F:57])[C:50]([F:56])([F:55])[C:51]([F:54])([F:53])[F:52])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]/[CH2:24][C@@H:25]2[CH2:42][C:41]3[CH:40]=[C:39]([O:43][CH3:44])[CH:38]=[CH:37][C:36]=3[C@@H:35]3[C@@H:26]2[C@H:27]2[C@@:31]([CH2:33][CH2:34]3)([CH3:32])[C@@H:30]([OH:45])[CH2:29][CH2:28]2)[C:3]1=[O:62].CN1[C@@H](C)[C@@H](C2C=CC=CC=2)N(C(=O)[C@@H](CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F)CCCCCC/C=C\C[C@@H]2CC3C=C(OC)C=CC=3[C@@H]3[C@@H]2[C@H]2[C@@](CC3)(C)[C@@H](O)CC2)C1=O>C(OCC)(=O)C.[C].[Pd]>[CH3:1][N:2]1[C@@H:6]([CH3:7])[C@@H:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:4]([C:14](=[O:61])[C@@H:15]([CH2:46][CH2:47][C:48]([F:59])([F:60])[C:49]([F:58])([F:57])[C:50]([F:56])([F:55])[C:51]([F:54])([F:53])[F:52])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C@@H:25]2[CH2:42][C:41]3[CH:40]=[C:39]([O:43][CH3:44])[CH:38]=[CH:37][C:36]=3[C@@H:35]3[C@@H:26]2[C@H:27]2[C@@:31]([CH2:33][CH2:34]3)([CH3:32])[C@@H:30]([OH:45])[CH2:29][CH2:28]2)[C:3]1=[O:62]

Participants

5

Reactant 2

HCID 86588683(4S,5R)-3,4-dimethyl-1-[(2R,9E)-11-(17beta-hydroxy-3-methoxyestra-1,3,5(10)-trien-7alpha-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoyl]-5-phenylimidazolidin-2-oneHCID 86600466(4S,5R)-3,4-dimethyl-1-[(2R,9Z)-11-(17beta-hydroxy-3-methoxyestra-1,3,5(10)-trien-7alpha-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoyl]-5-phenylimidazolidin-2-one

Product 1

HCID 86588682(4S,5R)-3,4-dimethyl-1-[(2R)-11-(17beta-hydroxy-3-methoxyestra-1,3,5(10)-trien-7alpha-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoyl]-5-phenylimidazolidin-2-oneYield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of (4S,5R)-3,4-dimethyl-1-[(2R,9E)-11-(17β-hydroxy-3-methoxyestra-1,3,5(10)-trien-7α-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoyl]-5-phenylimidazolidin-2-one and (4S,5R)-3,4-dimethyl-1-[(2R,9Z)-11-(17β-hydroxy-3-methoxyestra-1,3,5(10)-trien-7α-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoyl]-5-phenylimidazolidin-2-one (579 mg, 653 μmol) was dissolved in ethyl acetate (14 ml), followed by addition of 10% palladium carbon (58 mg) at room temperature. After purging with hydrogen, the reaction mixture was stirred for 19 hours at room temperature. After the reaction mixture was filtered through cellite, the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Kanto Kagaku, silica gel 60 (spherical, neutral), 40–100 μm, eluent: ethyl acetate/n-hexane=1/1) to give (4S,5R)-3,4-dimethyl-1-[(2R)-11-(17β-hydroxy-3-methoxyestra-1,3,5(10)-trien-7α-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoyl]-5-phenylimidazolidin-2-one (579 mg, Yield 100%).

Workup

  1. customAfter purging with hydrogen
  2. filtrationAfter the reaction mixture was filtered through cellite
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (Kanto Kagaku, silica gel 60 (spherical, neutral), 40–100 μm, eluent: ethyl acetate/n-hexane=1/1)

Sources & evidence

ORD record
ord-a32183f3522f4cdd8bda1ce10d991d48
Source dataset
uspto-grants-2007_03
Patent number
US07196081B2

Reaction notes

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