N-bromobutanimide → HCID 86738980, compound

HRID 434733Notes

Reaction equation

HRID 434733 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11](=[O:36])[CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][C@@H:18]1[C@@H:22](/[CH:23]=[CH:24]/[C@@H:25]([OH:33])[C:26]([CH3:32])([CH3:31])[CH2:27][CH2:28][CH2:29][CH3:30])[C@H:21]([OH:34])[CH2:20][C@@H:19]1[OH:35]>C(Cl)(Cl)Cl.O1CCCC1>[CH3:9][O:10][C:11](=[O:36])[CH2:12][CH2:13][CH2:14][CH:15]([Br:1])[CH:16]1[O:35][C@H:19]2[CH2:20][C@@H:21]([OH:34])[C@H:22](/[CH:23]=[CH:24]/[C@@H:25]([OH:33])[C:26]([CH3:32])([CH3:31])[CH2:27][CH2:28][CH2:29][CH3:30])[C@H:18]2[CH2:17]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13371596HCID 13371596, compound

Product 1

HCID 86738980HCID 86738980, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

By proceeding as described in Example 1 but using 800 mg of N-bromosuccinimide and 1.47 g of (5Z,13E)-(9α,11α,15R)-9,11,15-trihydroxy-16,16-dimethylprosta-5,13-dienoic acid methyl ester dissolved in a mixture of 40 ml of chloroform and 4 ml of tetrahydrofuran, there was obtained 1.24 g of the title compound having the following physical characteristics:

Sources & evidence

ORD record
ord-aab2dd0949d447b1941d57a7f709e569
Source dataset
uspto-grants-1983_08
Patent number
US04399147

Reaction notes

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