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US 2026/0159477 A1Published application
Processes for the Preparation of Alpha-Hydroxy Esters by an Acid Catalyzed Reaction of Alpha-Hydroxy Amides with Alcohols
AssigneeKemin Industries, Inc.
InventorsJatuporn Salaklang, Filip Nuyens, Ye Lao
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Abstract
The present disclosure provides processes for preparing an alpha-hydroxy ester from the corresponding nitrile through a hydroxy amide intermediate. Also provided are alpha-hydroxy esters prepared according to processes disclosed herein, compositions comprising the alpha-hydroxy esters, and methods of using the compositions.
Claims67
A method of preparing a compound of Formula (I):
- wherein
- R1 is chosen from H;
- C1-4 alkyl optionally substituted with —OH, —SH, —S—C1-4 alkyl, —CONH2, —NRaRb, or guanidino;
- phenyl optionally substituted with —OH or C1-4 alkyl;
- indolyl;
- and imidazolyl;
- wherein Ra and Rb are each independently H or C1-4 alkyl;
- and
- R2 is C1-8 alkyl or C4-7 cycloalkyl;
- wherein the method comprises reacting Reagent A with a compound of Formula (III):
- wherein Reagent A is a first acid, a base or a solid catalyst, and wherein the compound of Formula (III) is optionally purified prior to reacting with Reagent A, to form a compound of Formula (II):
- then reacting, in the presence of a second acid, R2OH with the compound of Formula (II) to form the compound of Formula (I).
9 more elements
A method of preparing a compound of Formula (I-A):
- comprising reacting a first acid with a compound of Formula (III-A):
- to form a compound of Formula (II-A):
- then reacting isopropyl alcohol with the compound of Formula (II-A) in the presence of HCl to form the compound of Formula (I-A).
A method of preparing a compound of Formula (I-A):
- comprising purifying a compound of Formula (III-A):
- reacting a base with the purified compound of Formula (III-A) to form a compound of Formula (II-A):
- then reacting isopropyl alcohol with the compound of Formula (II-A) in the presence of HCl to form the compound of Formula (I-A).
A method of preparing a compound of Formula (I-A):
- comprising purifying a compound of Formula (III-A):
- reacting a solid catalyst with the purified compound of Formula (III-A) to form a compound of Formula (II-A):
- then reacting isopropyl alcohol with the compound of Formula (II-A) in the presence of HCl to form the compound of Formula (I-A).
Dependencies are inferred from the claim text.