Estradiol → HCID 131725979, compound

HRID 1660711Notes

Reaction equation

HRID 1660711 reaction equation
[CH3:1][C@@:2]12[C@@H:18]([OH:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.[N+:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1)([O-:23])=[O:22]>C1(C)C=CC=CC=1>[N+:21]([C:24]1[CH:25]=[CH:26][C:27]([C:28]([O-:30])=[O:29])=[CH:31][CH:32]=1)([O-:23])=[O:22].[CH3:1][C@@:2]12[C@@H:18]([OH:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2

Participants

4

Reactant 2

HCID 5757EstradiolHCID 61084-Nitrobenzoic Acid

Product 1

HCID 131725979HCID 131725979, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Inversion of the configuration of the 17-position of oestradiol was achieved using a Misunobu reaction. The complex formed by triphenylphosphine and DEAD was reacted with the 3-O-benzyl-17-□-estradiol BLE99051 and p-nitrobenzoic acid at 80° C. in toluene to give the 3-O-benzyl-17-□-p-nitrobenzoate-estradiol BLE99053. Hydrolysis of the ester moiety of BLE99053 using potassium carbonate afforded cleanly the 3-O-benzyl-17-□-estradiol BLE99056 in a 84.5% yield.

Sources & evidence

ORD record
ord-055bcad9300748e394249e541090ddc7
Source dataset
uspto-grants-2011_10
Patent number
US08030296B2

Reaction notes

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