IP Library › Granted Patent US 8,163,933
Granted Patent B2
US 8,163,933 · App. 11/956,515 · Granted Apr 24, 2012

Clean, high-yield preparation of S,S and R,S amino acid isosteres

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Quick Facts
Patent No.
US 8,163,933
App. No.
11/956,515
Granted
Apr 24, 2012
Kind
B2
Abstract

The present invention provides compounds and methods that can be used to convert the intermediate halomethyl ketones (HMKs), e.g., chloromethyl ketones, to the corresponding S,S- and R,S-diastereomers. More particularly, the present invention provides: (1) reduction methods; (2) inversion methods; and (3) methods involving the epoxidation of alkenes. Using the various methods of the present invention, the R,S-epoxide and the intermediary compounds can be prepared reliably, in high yields and in high purity.

Claims (9)

1. A cyclic carbamate compound having the following general formula:

wherein:

R 1 is benzyl;

R 2 is a blocking group selected from Boc, Moc and Cbz; and

X 1 is a leaving group selected from chloro, bromo and fluoro groups.

2. The cyclic carbamate compound in accordance with claim 1 , wherein:

R 1 is benzyl;

R 2 is Boc; and

X 1 is a chloro or bromo group.

Assignments (12)
CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT STATEMENT THAT THIS DOCUMENT SERVES AS AN OATH/DECLARATION PREVIOUSLY RECORDED AT REEL: 047383 FRAME: 0438. ASSIGNOR(S) HEREBY CONFIRMS THE TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS. Recorded Nov 5, 2018
From: KEYBANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: AMPAC FINE CHEMICALS LLC
Reel/Frame 047422/0852 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Aug 31, 2018
From: KEYBANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: AMPAC FINE CHEMICALS LLC
Reel/Frame 047383/0437 →
GRANT OF SECURITY INTEREST IN PATENTS Recorded Aug 3, 2018
From: AMPAC FINE CHEMICALS LLC
To: KEYBANK NATIONAL ASSOCIATION
Reel/Frame 046703/0605 →
RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT R/F: 032365/0398 Recorded Dec 15, 2015
From: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
To: AMPAC FINE CHEMICALS LLC
Reel/Frame 037300/0399 →
PATENT RELEASE AND REASSIGNMENT (R/F 029370/0835) Recorded Feb 27, 2014
From: KEYBANK NATIONAL ASSOCIATION, AS AGENT
To: AMPAC FINE CHEMICALS LLC
Reel/Frame 032363/0222 →
SECURITY AGREEMENT Recorded Feb 27, 2014
From: AMPAC FINE CHEMICALS LLC
To: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 032365/0398 →
COLLATERAL ASSIGNMENT AND SECURITY INTEREST OF PATENTS Recorded Nov 28, 2012
From: AMPAC FINE CHEMICALS LLC
To: KEYBANK NATIONAL ASSOCIATION
Reel/Frame 029370/0835 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE FROM AMERICAN FINE CHEMICALS LLC TO AMPAC FINE CHEMICALS LLC PREVIOUSLY RECORDED ON REEL 029203 FRAME 0091. ASSIGNOR(S) HEREBY CONFIRMS THE RELEASE BY SECURED PARTY. Recorded Nov 5, 2012
From: WELLS FARGO BANK, NATIONAL ASSOCIATION
To: AMPAC FINE CHEMICALS LLC
Reel/Frame 029245/0597 →
RELEASE OF SECURITY INTEREST Recorded Oct 26, 2012
From: WELLS FARGO BANK, NATIONAL ASSOCIATION
To: AMERICAN FINE CHEMICALS LLC
Reel/Frame 029203/0091 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2011
From: MALIK, ASLAM A.; CLEMENT, TODD E.; PALANDOKEN, HASAN; ROBINSON, JAMES, III; STRINGER, JOY A.
To: AEROJET FINE CHEMICALS LLC
Reel/Frame 025905/0930 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2011
From: AEROJET FINE CHEMICALS LLC
To: AEROJET-GENERAL CORPORATION
Reel/Frame 025905/0936 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2011
From: AEROJET-GENERAL CORPORATION
To: AMPAC FINE CHEMICALS LLC
Reel/Frame 025905/0941 →