Benzoic anhydride → methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate

HRID 3031

Reaction equation

HRID 3031 reaction equation
I/[CH:2]=[CH:3]/[C@@H:4]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:18]([Li])([CH3:21])([CH3:20])[CH3:19].C([Cu])#CCCCC.C([C@H:34]1[CH2:38][C:37](=[O:39])[C:36]([S:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]([O:48][CH3:49])=[O:47])=[C:35]1O[SiH](C)C)(C)(C)C.[C:54]([O:62]C(=O)C1C=CC=CC=1)(=O)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>CN(C)P(N(C)C)N(C)C>[CH3:49][O:48][C:46](=[O:47])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][S:40][C:36]1[C@@H:35](/[CH:2]=[CH:3]/[C@@H:4]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[C@H:34]([O:10][Si:11]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:13])[CH3:12])[CH2:38][C:37]=1[O:39][C:54](=[O:62])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

7

Reactant 5

HCID 7167Benzoic anhydrideHCID 11111369(3S)-1-Iodo-3-(tert-butyldimethylsilyloxy)-1-octeneHCID 131720587(4R)-tert-butyldimethylsiloxy-2-(5-methoxycarbonylpentylthio)-2-cyclopenten-1-oneHCID 178418306HCID 178418306, compoundHCID 178418419C6H9Cu

Product 1

HCID 22883804methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoateYield 55.4%

Reagents, catalysts & solvents 1

HCID 15355Hexamethylphosphorous triamideSolvent

Procedure

Using as the materials and reagents (1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene (442 mg, 1.2 mmol), tert-butyllithium (1.54 mol/l, 1.56 ml, 2.4 mmol), 1-hexynylcopper (174 mg), hexamethylphosphorous triamide (436 μl), (4R)-tert-butyldimethylsiloxy-2-(5-methoxycarbonyl-pentylthio)-2-cyclopenten-1-one (373 mg, 1.0 mmol), and benzoic anhydride (661 mg), the same procedure was performed as in Example 1 to obtain methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate (239 mg, 33%).

Sources & evidence

ORD record
ord-76d32aafd0e142d0832c397f95f52a05
Source dataset
uspto-grants-1998_03
Patent number
US05731452

Linked notes

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