Method for the preparation of enantiomerically enriched amines

Details Method for the preparation of enantiomerically enriched amines Method for the preparation of enantiomerically enriched amines

2005-05-24

2005-05-24

Witz, Jean C. (Department: 1651)

Chemistry: molecular biology and microbiology

Process of utilizing an enzyme or micro-organism to destroy...

Resolution of optical isomers or purification of organic...

C435S129000, C435S228000

Reexamination Certificate

active

06897058

ABSTRACT:
Method for the preparation of an enantiomerically enriched acylated amine wherein a phenylacetic acid derivative is brought into contact with a mixture of enantiomers of an amine H2NCR1R2R3, in which R1, R2, R3are not equal to each other and each independently stand for H, CN, a whether or not substituted (cyclo)alkyl, ary-, alkylaryl or arylalkyl group, whether or not cyclic heteroalkyl or heteroaryl group with one or more N, O or S atoms or in which R1and R2(and R3) together with the C-atom to which they have been bound form a (bi)cyclic group that optionally contains one or more N, O of S atoms, in the presence of a Pen-G acylase derived fromAlcaligenes faecalis.And method for the preparation of enantiomerically enriched amine of formula H2NCR1R2R3, in which R1, R2, R3are as defined above, wherein an acylated amine is brought into contact with a Pen-G acylase originating fromAlcaligenes faecalis. Preferably enantiomerically enriched phenylglycine amide or an ester of p-hydroxyphenylglycine is applied as phenylacetic acid derivative.

REFERENCES:
patent: 6033823 (2000-03-01), Van Der Laan et al.
patent: 6465223 (2002-10-01), Nubling et al.
patent: 0176068 (1986-04-01), None
patent: 1009814 (2000-02-01), None
patent: 1010506 (2000-05-01), None
patent: WO 9402628 (1994-02-01), None
patent: WO 9850575 (1998-11-01), None
Guy et al. “Kinetic resolution of p-hydroxyphenyl acetamides by hydrolysis with Pen-G acylase” Bioorganic Med. Chem. Lett. (1993) 3(6): 1021-1044.*
Vedejs et al. “Heteroarene-2-sulfonyl chlorides (BtsCI; ThsCI): Reagents for nitrogen protection and >99% racemization-free phenylglycine activation with SOC12” J. Am. Chem. Soc. (1996) 118(4): 9796-9797.*
Bossi, A. et al., “Production of D-Phenylglycine from Racemic (D.L)-Phenylglycine via Isoelectrically-Trapped Penicillin G Acylase” Biotechnology and Bioengineering. Including: Symposium Biotechnology in Energy Production and Conservation 60(4):454-461 (1998).
Guranda, D.T. et al., “High Efficiency and Enantioselective Enzymatic Acylation of Amines in Aqueous Medium” Tetrahedron: Asymmetry 12(11):1645-1650 (2001).
Kajfez, F. et al., “A New Synthesis of Ampicillin and Related Investigations” Journal of Heterocyclic Chemistry 13(3):561-566 (1976).
Löffler, J. and Schobert, R., “2(3H)-Oxazolones from Alpha-Hydroxy Amides and Keteneylidenetriphenyl-Phosphorane Via Ylide Cascade” Liebigs Ann. Org. Bioorg. Chem. pp. 217-220 (1997).
Rossi, D. et al., “Approach to the Use of Benzyl Penicillin Acylase for Configurational Correlations of Amino Compounds” Journal of Organic Chemistry 43(13):2576-2581 (1978).
Svedas, V. et al., “Kinetic Study of Penicillin Acylase from Alcaligenes faecalis” FEBS Letters 417(3):414-418 (1997).
Van Langen, L.M. et al., “Penicillin Acylase-Catalyzed Resolution of Amines in Aqueous Organic Solvents” Tetrahedron: Asymmetry 11(22):4593-4600 (2000).

Affiliated with

Also associated with

Rating

Method for the preparation of enantiomerically enriched amines does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method for the preparation of enantiomerically enriched amines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for the preparation of enantiomerically enriched amines will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3393991