Claims
- 1. The 2-aminonitrile represented by formula 4 wherein n equals 0, 1, 2, 3 or 4 and R1 and R2 each independently represent an alkyl group with 1-10 carbon atoms or form a ring with 3 or 4 carbon atoms together with the oxygen atoms to which they are bound.
- 2. The 2-aminonitrile according to claim 1, wherein n equals 2 or 3.
- 3. A compound according to any one of claim 1, wherein R1 and R2 form a ring with 3 or 4 carbon atoms together with the oxygen atoms to which they are bound and the carbon atom to which the oxygen atoms are bound.
- 4. The 2-aminonitrile according to claim 1, prepared by a method comprising:converting the corresponding aldehyde represented by formula 2 wherein n equals 0, 1, 2, 3 or 4, with the aid of an alcohol, a diol or an orthoformate ester into the corresponding acetal-protected aldehyde represented by formula 3 with n as described above and R1 and R2 each independently represent an alkyl group with 1-10 carbon atoms or form a ring with 3 or 4 carbon atoms together with the oxygen atoms to which they are bound and the carbon atom to which the oxygen atoms areas bound,converting the acetal-protected an dehyde into the corresponding aminonitrile represented by formula 4 with n, R1 and R2 as described above, the conversion occurring in the presence of ammonia with the aid of a cyanide compound, andisolating the 2-aminonitrile from an aqueous phase using an organic solvent.
- 5. The 2-aminonitrile according to claim 4, wherein an organic layer containing the aminonitrile is dried to yield a free amino acid nitrile.
- 6. The 2-aminonitrile according to claim 4, wherein an organic layer containing the aminonitrile is treated with an acid gas to precipitate an aminonitrile acid salt.
- 7. The 2-aminonitrile prepared according to the method of claim 4, wherein the 2-aminonitrile is isolated via extraction.
Priority Claims (1)
Number |
Date |
Country |
Kind |
1007113 |
Sep 1997 |
NL |
|
RELATED APPLICATIONS
This application is a division of application Ser. No. 09/160,342, filed Sep. 25, 1998 now U.S. Pat. No. 6,133,002.
This application is a complete application that claims the benefit of U.S. Provisional Application No. 60/069,776 filed Dec. 16, 1997, the complete disclosure of which is incorporated herein by reference.
US Referenced Citations (4)
Foreign Referenced Citations (10)
Number |
Date |
Country |
37 02943 |
Aug 1987 |
DE |
0 052 201 |
Sep 1981 |
EP |
0 052 200 |
Sep 1981 |
EP |
0 179 523 |
Apr 1986 |
EP |
0 307 023 |
Aug 1988 |
EP |
0 383 403 |
Feb 1990 |
EP |
0 629 627 |
Jun 1994 |
EP |
0 672 665 |
Mar 1995 |
EP |
1 548 032 |
Aug 1976 |
GB |
48 039 416 |
Jun 1973 |
JP |
Non-Patent Literature Citations (3)
Entry |
Doelz et al., “Allysine Peptides and Derivatives”, Int. J. Peptide Protein Res. (1988), pp. 307-320. |
Rumbero et al., “Chemical Synthesis of Allysine Ethylene Acetal and Conversion in sutu Into 1-Piperideine-6-carboxylic Acid: Key Intermediate of the α-Aminoadipic Acid for β-Lactam Antibiotics Biosynthesis”, Biorganic & Medicinal Chemistry, vol. 3, No. 9, 1995, pp. 1237-1240. |
Sham et al., “Novel Non-basis Bioisostere of Hiidine Synthesized From L-Aspartic Acid”, J. Chem. Soc., Chem. Commun., 1987, pp. 1792-1793, vol. 23. |
Provisional Applications (1)
|
Number |
Date |
Country |
|
60/069776 |
Dec 1997 |
US |