IP Library Granted Patent US 7,595,419
Granted Patent B2
US 7,595,419 · App. 11/236,447 · Granted Sep 29, 2009

Process and intermediates for the preparation of 3-(amino)-3-cyclobutylmethyl-2-hydroxy-propionamide or salts thereof

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Quick Facts
Patent No.
US 7,595,419
App. No.
11/236,447
Granted
Sep 29, 2009
Kind
B2
Abstract

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.

Claims (17)

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”.

Assignments (1)
CHANGE OF NAME Recorded Aug 30, 2012
From: SCHERING CORPORATION
To: MERCK SHARP & DOHME CORP.
Reel/Frame 028884/0151 →