Process and intermediates for the preparation of 3-(amino)-3-cyclobutylmethyl-2-hydroxy-propionamide or salts thereof
View Patent ↗In one embodiment, the present application relates to a process of making a compound of formula I: and to certain intermediate compounds that are made within the process of making the compound of formula I.
1. A reaction mixture precipitate comprising predominantly the RR and SS enantiomer of Formula VIII;
wherein the precipitate is prepared by a process comprising:
(a) providing a reaction mixture by treating a DMSO solution of the compound of VII,
with a base in a suitable solvent and subsequently reacting it with peroxide; and
(b) precipitating the compounds of VIII RR and SS by adding an anti-solvent to the reaction mixture provided by step “a”.
2. The precipitate of claim 1 prepared by the process comprising:
a) reacting the compound of formula VI with
to yield a compound of formula VII:
b) hydrating the compound of formula VII in a reaction mixture comprising a low polarity solvent to yield a compound of formula VIII:
c) precipitating the RR and SS enantiomer of the compound of Formula VIII by adding water to the reaction mixture from step “b”.
3. A reaction mixture precipitate comprising predominantly the RS and SR enantiomer of Formula VIII;
Formula VIII RS Formula VIII SR
wherein the precipitate is prepared by a process comprising:
(a) separating the precipitate formed in Step “b” of claim 1 from the supernatant liquid by filtration;
(b) extracting the compounds of Formula VIII RS and VIII SR into ethylacetate;
(c) displacing the ethylacetate in the extract formed in Step “b” with n-butylacetate to form a butyl acetate solution comprising predominantly compounds of Formula VIII RS and VIII SR; and
(d) precipitating the compounds of compounds of Formula VIII RS and VIII SR from the butyl acetate solution provided in Step “c”.