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US 8,710,249 B2Granted
Maltol ether processes and intermediates
AssigneeShionogi & Co., Ltd.
InventorYasunori Aoyama
Life of this patent
Estimating the term…
Abstract
Novel processes and intermediates are provided according to the general reaction scheme: Formula I, II, III, IV (I), (II), (III), (IV) utilizing a ruthenium catalyst in an oxidative cleavage of the triene 4 whereby an aldehyde may be produced and optionally taken on to a carboxylic acid 5: Formula V (V)
Claims9
A process of producing an aldehyde of formula 1,
- which comprises the steps of:
- (i) reacting a pyrone of formula 2 with an aldehyde of formula A-CHO to produce an alcohol of formula 3;
- (ii) reacting the alcohol of the formula 3 with a dehydrating reagent to produce a triene of formula 4;
- and
- (iii) reacting the triene of the formula 4 with an oxidating reagent to produce the aldehyde of the formula 1,
- wherein:
- P1 is hydrogen or a hydroxyl protecting group;
- Rx is halogen or R2—X—NR1—C(O)—;
- R1 is hydrogen or lower alkyl;
- X is a single bond, a heteroatom group selected from the group consisting of O, S, SO, SO2 and NH, a loweralkylene or a loweralkylene wherein each alkyl may be intervened by a heteroatom;
- R2 is optionally substituted aryl;
- and
- A is aryl.
10 more elements
An alcohol of the following formula 3:
- wherein:
- P1 is hydrogen or a hydroxyl protecting group;
- Rx is halogen or R2—X—NR1—C(O)—;
- R1 is hydrogen or lower alkyl;
- X is a single bond, a heteroatom group selected from the group consisting of O, S, SO, SO2 and NH, a loweralkylene or a loweralkylene wherein each alkyl may be intervened by a heteroatom;
- R2 is optionally substituted aryl;
- and
- A is aryl.
5 more elements
A triene of the following formula 4:
- wherein:
- P1 is hydrogen or a hydroxyl protecting group;
- Rx is halogen or R2—X—NR1—C(O)—;
- R1 is hydrogen or lower alkyl;
- X is a single bond, a heteroatom group selected from the group consisting of O, S, SO, SO2 and NH, a loweralkylene or lowerlalkylene a loweralkylene wherein each alkyl may be intervened by a heteroatom;
- R2 is optionally substituted aryl;
- A is aryl;
- and
- the wavy line bond is either cis or trans.
6 more elements
A process of producing a carboxylic acid of formula 5,
- which comprises the steps of:
- (i) reacting a pyrone of formula 2 with an aldehyde of formula A-CHO to produce an alcohol of formula 3;
- (ii) reacting the alcohol of the formula 3 with a dehydrating reagent to produce a triene of formula 4;
- (iii) reacting the triene of the formula 4 with an oxidating reagent to produce an aldehyde of formula 1:
- and
- (iv) oxidizing the aldehyde of the formula 1 to produce the carboxylic acid of the formula 5,
- wherein:
- P1 is hydrogen or a hydroxyl protecting group;
- Rx is halogen or R2—X—NR1—C(O)—;
- R1 is hydrogen or lower alkyl;
- X is a single bond, a heteroatom group selected from the group consisting of O, S, SO, SO2—and NH, a loweralkylene or lowerlalkylene a loweralkylene wherein each alkyl may be intervened by a heteroatom;
- R2 is optionally substituted aryl;
- and
- A is aryl.
11 more elements
A process of producing a carboxylic acid of formula 5,
- which comprises the steps of:
- (iii) reacting a triene of formula 4 with an oxidating reagent to produce an aldehyde of formula 1;
- and
- (iv) oxidizing the aldehyde of the formula 1 to produce the carboxylic acid of the formula 5,
- wherein:
- P1 is hydrogen or a hydroxyl protecting group;
- Rx is halogen or R2—X—NR1—C(O)—;
- R1 is hydrogen or lower alkyl;
- X is a single bond, a heteroatom group selected from the group consisting of O, S, SO, SO2 and NH, a loweralkylene or a loweralkylene wherein each alkyl may be intervened by a heteroatom;
- R2 is optionally substituted aryl;
- and
- A is aryl.
9 more elements
Dependencies are inferred from the claim text.