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1. (WO1998049133) PROCESS FOR ESTERIFICATION OF AMINO ACIDS AND PEPTIDES
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/1998/049133 International Application No.: PCT/NL1998/000227
Publication Date: 05.11.1998 International Filing Date: 23.04.1998
Chapter 2 Demand Filed: 05.10.1998
IPC:
C07C 227/18 (2006.01) ,C07C 305/06 (2006.01) ,C07D 207/16 (2006.01) ,C07K 1/107 (2006.01) ,C07K 5/06 (2006.01) ,C07K 5/075 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
227
Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
14
from compounds containing already amino and carboxyl groups or derivatives thereof
18
by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
305
Esters of sulfuric acids
02
having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
04
being acyclic and saturated
06
Hydrogenosulfates
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
207
Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
02
with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
04
having no double bonds between ring members or between ring members and non-ring members
10
with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
16
Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
K
PEPTIDES
1
General processes for the preparation of peptides
107
by chemical modification of precursor peptides
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
K
PEPTIDES
5
Peptides having up to four amino acids in a fully defined sequence; Derivatives thereof
04
containing only normal peptide links
06
Dipeptides
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
K
PEPTIDES
5
Peptides having up to four amino acids in a fully defined sequence; Derivatives thereof
04
containing only normal peptide links
06
Dipeptides
072
the side chain of the first amino acid containing more carboxyl groups than amino groups, or derivatives thereof, e.g. Asp, Glu, Asn
075
Asp-Phe; Derivatives thereof, e.g. aspartame
Applicants:
DSM N.V. [NL/NL]; Het Overloon 1 NL-6411 TE Heerlen, NL (AL, AM, AT, AU, AZ, BA, BB, BE, BF, BG, BJ, BR, BY, CA, CF, CG, CH, CI, CM, CN, CU, CY, CZ, DE, DK, EE, ES, FI, FR, GA, GB, GE, GH, GM, GN, GR, HU, ID, IE, IL, IS, IT, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MC, MD, MG, MK, ML, MN, MR, MW, MX, NE, NL, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, SN, SZ, TD, TG, TJ, TM, TR, TT, UA, UG, UZ, VN, YU, ZW)
BOESTEN, Wilhelmus, Hubertus, Joseph [NL/NL]; NL (UsOnly)
QUAEDFLIEG, Peter, Jan, Leonard, Mario [NL/NL]; NL (UsOnly)
Inventors:
BOESTEN, Wilhelmus, Hubertus, Joseph; NL
QUAEDFLIEG, Peter, Jan, Leonard, Mario; NL
Agent:
JACOBS, Monique, Sophie, Nicole; Octrooibureau DSM P.O. Box 9 NL-6160 MA Geleen, NL
Priority Data:
100590125.04.1997NL
Title (EN) PROCESS FOR ESTERIFICATION OF AMINO ACIDS AND PEPTIDES
(FR) PROCEDE D'ESTERIFICATION DES ACIDES AMINES ET DES PEPTIDES
Abstract:
(EN) Process for the esterification of an amino acid or peptide in which the amino acid or peptide is converted into the corresponding ester in the presence of a hydrosulphate having the general formula ROSO3H, where R represents an alkyl group, with the hydrosulphate being prepared, in the presence of the amino acid or peptide, from chlorosulphonic acid and an alcohol having the general formula ROH, where R has the same meaning as above. The chlorosulphonic acid to amino acid or peptide molar ratio preferably is between 0.8 and 2.0, in particular between 1.0 and 1.3. A primary alcohol, in particular methanol, is preferably used as alcohol. The amino acid used may be for example an $g(a)-amino acid chosen from the group comprising p-hydroxyphenylglycine, phenylglycine, phenylalanine, tyrosine, proline and valine; L-alanyl-L-proline or an ester of L-aspartyl-L-phenylalanine, for example, may be used as peptide.
(FR) Procédé permettant d'estérifier un acide aminé ou un peptide, selon lequel on convertit ledit acide aminé ou peptide en l'ester correspondant, en présence d'un hydrosulfate de formule générale ROSO3H, dans laquelle R représente un groupe alkyle. On prépare l'hydrosulfate, en présence de l'acide aminé ou du peptide, à partir de l'acide chlorosulfonique et d'un alcool de formule générale ROH, dans laquelle R a la même signification que ci-dessus. Le rapport molaire entre l'acide chlorosulfonique et l'acide aminé ou le peptide est de préférence compris entre 0,8 et 2,0, en particulier entre 1,0 et 1,3. On utilise de préférence comme alcool un alcool primaire, notamment le méthanol. L'acide aminé utilisé peut être par exemple un $g(a)-amino acide choisi dans le groupe comprenant la p-hydroxyphénylglycine, la phénylglycine, la phénylalanine, la tyrosine, la proline et la valine. Le peptide utilisé peut être par exemple la L-alanyl-L-proline ou un ester de la L-aspartyl-L-phénylalanine.
Designated States: AL, AU, BA, BB, BG, BR, CA, CN, CU, CZ, EE, GE, HU, ID, IL, IS, JP, KP, KR, LC, LK, LR, LT, LV, MG, MK, MN, MX, NO, NZ, PL, RO, SG, SI, SK, SL, TR, TT, UA, US, UZ, VN, YU
African Regional Intellectual Property Organization (ARIPO) (GH, GM, KE, LS, MW, SD, SZ, UG, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: Dutch (NL)
Also published as:
EP0977726US6222013JP2001524107 DE000069806747AU1998070853