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US 2003/0120096 A1Published application
Process for the preparation of metal alkoxides
AssigneeFlorida State University
InventorRobert A. Holton
Life of this patent
Estimating the term…
Abstract
A process for preparing N-acyl, N-sulfonyl and N-phosphoryl substituted isoserine esters in which a metal alkoxide is reacted with a β-lactam.
Claims20
A process for the preparation of a substituted isoserine ester having the formula
- 51
- comprising reacting a β-lactam with a metal alkoxide, the β-lactam having the formula
- 52
- and the metal alkoxide having the formula
- MOCE1E2E3
- wherein
- R1 is —OR6, —SR7, or —NR8R9;
- R2 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl;
- R3 and R4 are independently hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or acyl, provided, however, that R3 and R4 are not both acyl;
- R5 is —COR10, —COOR10, —COSR10, —CONR8R10, —SO2R11, or —POR12R13,
- R6 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, hydroxy protecting group, or a functional group which increases the water solubility of the taxane derivative,
- R7 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or sulfhydryl protecting group,
- R8 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or tieteroaryl;
- R9 is an amino protecting group;
- R10 is alkyl, alkenyl, alkynyl, aryl, or heteroaryl,
- R11 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, —OR10, or —NR8R14,
- R12 and R13 are independently alkyl, alkenyl, alkynyl, aryl, heteroaryl, —OR10, or —NR8R14,
- R14 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl;
- and
- E1, E2 and E3 are independently hydrogen, hydrocarbon or cyclic, provided, at least one of E1, E2 and E3 is other than hydrogen.
17 more elements
A process for the preparation of a taxane derivative comprising:
- providing a metal alkoxide having the formula MOCE1E2E3,
- reacting the metal alkoxide with a β-lactam to form an intermediate, the β-lactam having the formula:
- 54
- wherein
- M is a metal,
- one of E1, E2 and E3 is hydrogen and the other two of E1, E2 and E3 together with the carbon to which they are attached comprise a polycyclic skeleton,
- R1 is —OR6, —SR7, or —NR8R9;
- R2 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl;
- R3 and R4 are independently hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or acyl, provided, however, that R3 and R4 are not both acyl;
- R5 is —COR10, —COOR10, —COSR10, —CONR8R10, —SO2R11, or —POR12R13,
- R6 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, hydiroxy protecting group, or a functional group which increases the water solubility of the taxane derivative,
- R7 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or sulfhydryl protecting group,
- R8 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl;
- R9 is an amino protecting group;
- R10 is alkyl, alkenyl, alkynyl, aryl, or heteroaryl,
- R11 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, —OR10, or —NR8R14,
- R12 and R13 are independently alkyl, alkenyl, alkynyl, aryl, heteroaryl, —OR10, or —NR8R14,
- R14 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl;
- and
- converting said intermediate to the taxane derivative.
17 more elements
A process for the preparation of a taxane derivative comprising:
- providing a metal alkoxide having the formula MOCE1E2E3,
- reacting the metal alkoxide with a β-lactam to form an intermediate, the β-lactam having the formula:
- 58
- wherein
- M is a metal,
- one of E1, E2 and E3 is hydrogen and the other two of E1, E2 and E3 together with the carbon to which they are attached comprise a polycarbocyclic skeleton,
- R1 is —OR6,
- R2 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl;
- R3 and R4 are independently hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or acyl, provided, however, that R3 and R4 are not both acyl;
- R5 is —COR10, —COOR10, —COSR10, —CONR8R10, —SO2R11, or —POR12R13,
- R6 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, hydroxy protecting group, or a functional group which increases the water solubility of the taxane derivative,
- R7 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or sulfhydryl protecting group,
- R8 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl;
- R9 is an amino protecting group;
- R10 is alkyl, alkenyl, alkynyl, aryl, or heteroaryl,
- R11 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, —OR10, or —NR8R14,
- R12 and R13 are independently alkyl, alkenyl, alkynyl, aryl, heteroaryl, —OR10, or —NR8R14,
- R14 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl;
- and
- converting said intermediate to the taxane derivative.
17 more elements
Dependencies are inferred from the claim text.