Tetrabutylammonium Fluoride → 1-p-methoxybenzyl-3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone

HRID 65438Notes

Reaction equation

HRID 65438 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]([CH2:14][S:15]([C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:17])=[O:16])[C:9](=[O:13])[C@@H:10]2[O:12][CH2:11]2)=[CH:5][CH:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[C@H:14]([S:15]([C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:17])=[O:16])[C@@H:10]([CH2:11][OH:12])[C:9]2=[O:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57103465HCID 57103465, compound

Product 1

HCID 186047721-p-methoxybenzyl-3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Analogously to Example 8b, from 1.71 g (5 mmol) of N-p-methoxybenzyl-N-tert.-butylsulphonylmethyl-(R)-glycidic acid amide in THF, by reaction with dehydrated tetra-n-butylammonium fluoride in the presence of activated molecular sieve, there is obtained the title compound in the form of a crude product which is chromatographed over silica gel using toluene/ethyl acetate (4:1) and (2:1). The pure title compound is obtained.

Sources & evidence

ORD record
ord-24a9b3239f7040c2b56ebbbd03b3ee5f
Source dataset
uspto-grants-1986_09
Patent number
US04614614

Reaction notes

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