Process for preparing (1'R,3S)-3-(1'-hydroxyethyl)-azetidin-2-on

Details Process for preparing (1'R,3S)-3-(1'-hydroxyethyl)-azetidin-2-on Process for preparing (1'R,3S)-3-(1'-hydroxyethyl)-azetidin-2-on

1991-11-08

1993-04-20

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

540200, C07D20508, C07B 4306

Patent

active

052044610

ABSTRACT:
A process for preparing (1'R,3S)-3-(1'-hydroxyethyl)-azetidin-2-one or a derivative thereof represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a hydroxyl-protective group, is disclosed, comprising reacting (2S,3R)-2-aminomethyl-3-hydroxybutyric acid or a derivative thereof represented by formula (II): ##STR2## wherein R.sup.1 is as defined above, with a sulfenamide represented by formula (III): ##STR3## wherein R.sup.2 represents ##STR4## and R.sup.3 and R.sup.4 each represent a hydrogen atom or a cyclic or acyclic hydrocarbon group, provided that they do not simultaneously represent a hydrogen atom, or R.sup.3 and R.sup.4 are taken together with the adjacent nitrogen atom to form a heterocyclic group, and triphenylphosphine. The reaction yield is high, and the sulfenamide (III) used as a lactamization reagent is cheap and can be recovered after the reaction.

REFERENCES:
patent: 5037974 (1991-08-01), Loewe
Kobayashi, JACS 103, 2406-8 (1981).

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