Phthalimide → Methyl 4-{3-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethoxy]-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl}pentanoate

HRID 1280864Notes

Reaction equation

[OH:1][CH:2]1[CH:18]2[CH:10]([CH2:11][CH:12]([OH:28])[C:13]3([CH3:27])[CH:17]2[CH2:16][CH2:15][CH:14]3[CH:19]([CH3:26])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:9]2([CH3:29])[CH:4]([CH2:5][CH:6]([O:30][CH2:31][CH2:32]O)[CH2:7][CH2:8]2)[CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:53]1(=[O:63])[NH:57][C:56](=[O:58])[C:55]2=[CH:59][CH:60]=[CH:61][CH:62]=[C:54]12.C([O-])(O)=O.[Na+]>C1COCC1>[O:58]=[C:56]1[C:55]2[C:54](=[CH:62][CH:61]=[CH:60][CH:59]=2)[C:53](=[O:63])[N:57]1[CH2:32][CH2:31][O:30][CH:6]1[CH2:5][CH:4]2[C:9]([CH3:29])([CH:10]3[CH:18]([CH:2]([OH:1])[CH2:3]2)[CH:17]2[C:13]([CH3:27])([CH:14]([CH:19]([CH3:26])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:15][CH2:16]2)[CH:12]([OH:28])[CH2:11]3)[CH2:8][CH2:7]1

Participants

Conditions

Temperature: 45 °C

Procedure

1.5 g of methyl 4-[7,12-Dihydroxy-3-(2-hydroxyethoxy)-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl]pentanoate, 950 mg of triphenylphosphine and 550 mg of phthalimide are warmed to 45° C. in 26 ml of THF and 1.14 ml of diethyl azodicarboxylates are added dropwise at this temperature. The reaction mixture is stirred at 45° C. for 2 hours, then poured into 200 ml of a semiconcentrated aqueous NaHCO3 solution and extracted 3 times using 200 ml of EA each time. The extract is dried over Na2SO4 and the solvent is removed in vacuo. Chromatography on silica gel using t-butyl methyl ether (MTB) yields 1.76 g of a viscous oil

Workup

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

Sources & evidence

ORD record: ord-ed5931851f9247eea554b83df32809c1
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451781B1

Reaction notes

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