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US 11,505,522 B2Granted
Processes for the preparation of (S)-tert-butyl 4,5- diamino-5-oxopentanoate
AssigneeCelgene Corporation
InventorsJohn F. Traverse, Michael J. Zacuto, Weihong Zhang, Kirsten Faye Johnson, Maryll E. Geherty, Christopher Marton
Life of this patent
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Abstract
Provided are processes for the preparation of (S)-tert-butyl 4,5-diamino-5-oxopentanoate, or a salt, solvate, hydrate, enantiomer, mixture of enantiomers, or isotopologue thereof. Also provided are solid forms of various intermediates and products obtained from the processes.
Claims20
A process for preparing a compound of Formula (I-rac):
- or a salt, solvate, hydrate, enantiomer, or isotopologue thereof, comprising
- (a) contacting a compound of Formula (XI):
- or a solvate, hydrate, or isotopologue thereof, wherein R5 is —CONH2, —CN, or —CO2R6, and R6 is a C1-10 alkyl, with tert-butyl acrylate in the presence of a base to provide a compound of Formula (XII):
- or a solvate, hydrate, or isotopologue thereof;
- (b) transforming the compound of Formula (XII), or a solvate, hydrate, or isotopologue thereof, to a compound of Formula (XIII):
- or a solvate, hydrate, or isotopologue thereof, in the presence of an acid;
- (c) when R5 is not —CONH2, transforming the R5 group to —CONH2 to provide a compound of Formula (I-rac), or a solvate, hydrate, or isotopologue thereof, wherein the —NH2 group in the compound of Formula (XIII), or a solvate, hydrate, or isotopologue thereof, is optionally protected and deprotected in step (c);
- (d) optionally separating the compound of Formula (I-rac), or a solvate, hydrate, or isotopologue thereof, to provide a compound of Formula (I):
- or a solvate, hydrate, or isotopologue thereof, via a chiral separation condition;
- and
- (e) optionally converting the compound of Formula (I), or a solvate, hydrate, or isotopologue thereof, to a salt of the compound.
8 more elements
A process for preparing a compound of Formula (I-rac):
- or a salt, solvate, hydrate, enantiomer, or isotopologue thereof, comprising
- (b) transforming a compound of Formula (XII):
- or a solvate, hydrate, or isotopologue thereof, wherein R5 is —CONH2, —CN, or —CO2R6, and R6 is a C1-10 alkyl, to a compound of Formula (XIII):
- or a solvate, hydrate, or isotopologue thereof, in the presence of an acid;
- (c) when R5 is not —CONH2, transforming the R5 group to —CONH2 to provide a compound of Formula (I-rac), or a solvate, hydrate, or isotopologue thereof, wherein the —NH2 group in the compound of Formula (XIII), or a solvate, hydrate, or isotopologue thereof, is optionally protected and deprotected in step (c);
- (d) optionally separating the compound of Formula (I-rac), or a solvate, hydrate, or isotopologue thereof, to provide a compound of Formula (I):
- or a solvate, hydrate, or isotopologue thereof, via a chiral separation condition;
- and
- (e) optionally converting the compound of Formula (I), or a solvate, hydrate, or isotopologue thereof, to a salt of the compound.
6 more elements
Dependencies are inferred from the claim text.