KR840006337A - Method for preparing azetidinyl sulfonic acid and derivatives thereof - Google Patents

Abstract

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Description

Method for preparing azetidinyl sulfonic acid and derivatives thereof

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Claims (15)

The compound of formula (V) is then cyclized to obtain the product of formula (VI), which is methoxylated with a halogenated reagent and a methoxylation reagent to give R ₂ a methoxy group. And then the amino protecting group is removed from this product to obtain a product wherein R ₁ is hydrogen, and the product is acylated to obtain a product wherein R ₁ is acyl group, or β-lactam of formula (I) Methods of preparing their salts or esters. In the above formula, R _{1 is an} acyl group, hydrogen or amino protecting group, R ₂ is hydrogen or methoxy [R ₂ in formula (VI) is hydrogen]. R ₃ and R ₄ are the same as or different from each other, and each is hydrogen, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a phenyl group, a substituted phenyl group or a 4, 5, 6 or 7 membered heterocyclic group, or R ₃ and If any one of R ₄ is hydrogen, the other is an azido group, a halomethyl group, a dihalomethyl group, a trihalomethyl group, an alkoxycarbonyl group, a 2-phenylethenyl group, a 2-phenylethynyl group, a carboxyl group, -CH _2- X ₁ , -SX ₂ , or -NX ₆ X ₇ (wherein X ₁ is an azido group, amino group, (-NH ₂ ), hydroxy group, alkanoylamino group, alkylsulfonyloxy group, phenylsulfonyloxy group, (substituted phenyl) sulfonyloxy group, phenyl group, substituted phenyl group , Cyano group, -SX ₂ or -OX ₂ and X ₂ is an alkyl group, substituted alkyl group, phenyl group, substituted phenyl group, phenylalkyl group, (substituted phenyl) alkyl group, alkanoyl group, substituted alkanoyl group, phenylcarbonyl group, (substituted phenyl) carbonyl group Or heteroarylcarbonyl, and when one of X ₃ and X ₄ is hydrogen, the other is hydrogen or an alkyl group, or X ₃ and X ₄ combine with the carbon atom to which they are attached to form a cycloalkyl group, X ₅ is a formomyl group, an alkanoyl group, a phenylcarbonyl group, a (substituted phenyl) carbonyl group, a phenylalkylcarbonyl group, a (substituted phenyl) alkylcarbonyl group, a carboxyl group, an alcoholic carbonyl group, an aminocarbonyl group (NH ₂ -OC-), (substituted amino) carbonyl group or Is a cyano group (C = N), A is -CH = CH-, CH ₂ -CH = CH ₁ ,-(CH ₂ ) _n -,-(CH ₂ ) _n , -O-,-(CH ₂ ) _n '-NH- or-(CH ₂ ) _n ' -S-CH ₂ , n is 0,1,2 or 3, n 'is 1 or 2, X ₆ and X ₇ are the same as or different from each other Hydrogen or an alkyl group, wherein X ₆ is hydrogen, X ₇ is an amino group, a substituted amino group, an acylamino group or an alkoxy group) R ₅ and R ₆ are the same as or different from each other, and each hydrogen, alkyl group alkenyl group, alkynyl group, phenyl group, A substituted phenyl group, a cycloalkyl group, or R ₇ ', or R ₅ and R ₆ combine with the carbon atom to which they are attached to form a cycloalkyl group or R ₇ ', or one of R ₅ and R ₆ is hydrogen and the other an azido group, a halo group, a methyl group to a methyl group, and a trihalomethyl-dihalo, Al-butoxycarbonyl group, a 2-phenylethyl group, Te, Ti in the 2-phenyl group, a carboxyl _{group, -CH 2 X 1 -, -SX} 2, -OX 2 or to be.) The process according to claim 1, wherein R ₂ is hydrogen. The process according to claim 2, wherein any one of R ₃ and R ₄ is not hydrogen. The process according to claim 2, wherein R ₃ is hydrogen and R ₄ is a methyl group. The process according to claim 2, wherein R ₃ is a methyl group and R ₄ is hydrogen. The process according to claim 2, wherein R ₅ and R ₆ are each hydrogen. The method according to claim 2, wherein R ₅ and R ₅ are each a methyl group. The process according to claim 2, wherein R ₁ is a (Z) -2-amino-α-[(1-carboxy-1-methylethoxy) imino] -4-thiazoleacetyl group. The process according to claim 1, wherein R ₂ , R ₅ and R ₆ are each hydrogen and one of R ₃ and R ₄ is an alkyl group and the other is hydrogen. The process according to claim 3, wherein R ₂ , R ₃ , R ₅ and R ₆ are each hydrogen and each R ₄ methyl group. 4. A process according to claim 3 wherein R ₂ , R ₄ , R ₅ and R ₆ are each hydrogen and R ₃ is a methyl group. The process according to claim 1, wherein R ₁ is hydrogen. A process according to claim 1 wherein R ₁ is an amino protecting group. The product of claim 1, wherein the product is [3S- [3α (Z), 4β]]-2-[[[1- (2-amino-4-thiazolyl) -2-[[4-methyl-2-oxo -1- (sulfomethoxy) -3-azetidinyl] amino] -2-oxoethylidene] amino] oxy] -2-methylpropanoic acid. The process according to claim 1, wherein the product is [3S- (3α, 4β)]-1-sulfomethoxy-3-amino-4-methyl-2-oxo-1-azetidine. ※ Note: The disclosure is based on the initial application.