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US 12,759,976 B2Granted
Processes for the preparation of alpha-hydroxy esters by esterification of alpha-hydroxy acids
AssigneeKemin Industries, Inc.
InventorsShengshu Huang, Fangyi Li, Li Xu, Filip Nuyens, Ye Lao, Jatuporn Salaklang, Zhuo Tang
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Abstract
The present disclosure provides processes for preparing an alpha-hydroxy ester from the corresponding alpha-hydroxy acid by transesterification. Also provided are alphahydroxy esters prepared according to processes disclosed herein and compositions comprising the alpha-hydroxy esters.
Claims18
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;
- comprising a) reacting at room temperature a compound of formula RxC(O)Cl with a compound of formula R2OH to form a reagent of Formula (A):
- and to form in-situ an acid catalyst;
- wherein Rx is chosen from H, C1-4 alkyl, and CH2—CH—;
- and
- b) reacting, at a temperature of 80° C. to 90° C., a compound of Formula (II):
- with the reagent of Formula (A) in the presence of the in-situ generated acid catalyst.
12 more elements
A method of preparing a compound of Formula (I-A):
- comprising reacting acetyl chloride with isopropyl alcohol to form isopropyl acetate;
- and
- reacting a compound of Formula (II-A):
- with isopropyl acetate.
1 more element
Dependencies are inferred from the claim text.