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US 11,639,326 B2Granted
Continuous flow synthesis of ibuprofen
AssigneeSRI International
InventorsNathan Collins, Jeremiah Malerich, Judy Szeto, Joseph A. Kozocas
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Abstract
This disclosure generally relates to methods of making ibuprofen, naproxen, and derivatives thereof. This disclosure also generally relates to compounds made by the disclosed methods. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
Claims16
A method for preparing a cyano compound having a structure represented by a formula:
- wherein n is selected from 0, 1, 2, 3, and 4;
- wherein each of R1a and R1b, when present, is independently selected from hydrogen and C1-C4 alkyl;
- wherein R2 is selected from hydrogen and C1-C4 alkyl;
- and
- wherein each of R3a, R3b, R3c, R3d, and R3e is independently selected from hydrogen, halogen, —OH, —NH2, —NO2, —CN, C1-C4 alkyl, and C1-C4 alkoxy;
- or wherein any two of R3a, R3b, R3c, R3d, and R3e together comprise a structure represented by a formula:
- and
- wherein each of R4a, R4b, R4c, and R4d, when present, is independently selected from hydrogen, halogen, —OH, —NH2, —NO2, —CN, C1-C4 alkyl, and C1-C4 alkoxy,
- the method comprising the steps of:
- (a) reducing a carbonyl compound having a structure represented by a formula:
- thereby producing an alcohol having a structure represented by a formula:
- (b) converting a hydroxyl group on the alcohol to a leaving group, thereby producing a compound having a structure represented by a formula:
- wherein LG is a leaving group;
- and
- (c) displacing the leaving group with a nucleophilic cyanide reagent, thereby producing the cyano compound,
- wherein step (b) is performed in flow.
13 more elements
A method for preparing a cyano compound having a structure:
- the method comprising the steps of:
- (a) reducing a carbonyl compound having a structure:
- thereby producing an alcohol having a structure:
- (b) converting a hydroxyl group on the alcohol to a leaving group, thereby producing a compound having a structure:
- wherein LG is selected from chloro and mesyl;
- and
- (c) displacing the leaving group with a nucleophilic cyanide reagent, thereby producing the cyano compound,
- wherein steps (a), (b), and (c) are performed sequentially in flow.
5 more elements
A method for preparing a cyano compound having a structure represented by a formula:
- wherein n is selected from 0, 1, 2, 3, and 4;
- wherein each of R1a and R1b, when present, is independently selected from hydrogen and C1-C4 alkyl;
- wherein R2 is selected from hydrogen and C1-C4 alkyl;
- and
- wherein each of R3a, R3b, R3c, R3d, and R3e is independently selected from hydrogen, halogen, —OH, —NH2, —NO2, —CN, C1-C4 alkyl, and C1-C4 alkoxy;
- or wherein any two of R3a, R3b, R3c, R3d, and R3e together comprise a structure represented by a formula:
- and
- wherein each of R4a, R4b, R4c, and R4d, when present, is independently selected from hydrogen, halogen, —OH, —NH2, —NO2, —CN, C1-C4 alkyl, and C1-C4 alkoxy,
- the method comprising the steps of:
- (a) reducing a carbonyl compound having a structure represented by a formula:
- thereby producing an alcohol having a structure represented by a formula:
- (b) converting a hydroxyl group on the alcohol to a leaving group, thereby producing a compound having a structure represented by a formula:
- wherein LG is a leaving group;
- and
- (c) displacing the leaving group with a nucleophilic cyanide reagent, thereby producing the cyano compound,
- wherein step (b) is performed with no work-up.
13 more elements
Dependencies are inferred from the claim text.