Preparation of protected amines or alkylated amino acids
AssigneeBASF Aktiengsellschaft
InventorsThomas Rosenau, Wolf-Dieter Habicher, Chen-Loung Chen
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Abstract
The present invention relates to a process for preparing protected amines or amino acids. The invention furthermore relates to the use of tocopheryl radicals or radicals derived therefrom as protective groups for amines and amino acids, and to compounds obtained in this process as intermediates and to processes for preparing dipeptides and oligopeptides.
Claims7
A process for introducing protective groups of the formula II ##STR16## where Y is --O--R.sup.1 or --NR.sub.2.sup.1, where
- R.sup.1 is H or C.sub.1 -C.sub.6 -alkyl and, in the case where Y=O, R.sup.1 is also --Si(C.sub.1 -C.sub.3 -alkyl).sub.3 or ##STR17## where R.sup.6 =C.sub.1 -C.sub.3 -alkyl, R.sup.2 and R.sup.3 are each, independently of one another, H, C.sub.1 -C.sub.3 -alkyl, --O--R.sup.6, --O-aryl or aryl, where R.sup.6 =C.sub.1 -C.sub.3 -alkyl,
- R.sup.4 and R.sup.5 are each, independently of one another, C.sub.1 -C.sub.20 -alkyl, aryl, C.sub.1 -C.sub.3 -alkyl-aryl, --CO--R.sup.7 or --CO.sub.2 R.sup.7 where R.sup.7 =H or C.sub.1 -C.sub.20 -alkyl, and
- X is Cl, Br, --OSO.sub.3 R.sup.0 where R.sup.0 =C.sub.1 -C.sub.6 -alkyl, aryl, C.sub.1 -C.sub.3 -alkyl-aryl or C.sub.1 -C.sub.3 -alkylene-aryl
- into amines or amino acids which comprises:
- reacting the amines or amino acids with a compound of the formula I ##STR18## where Y and R.sup.2 to R.sup.5 have the above meanings at a temperature of from -40 .degree. C. to +100.degree. C.
A process for preparing secondary amines or monoalkylated amino acids by the alkylation of primary amines or amino acids which comprises:
- reacting the primary amines or amino acids before the alkylation with a compound of the formula I ##STR23## where Y is --O--R.sup.1 or --NR.sub.2.sup.1, where
- R.sup.1 is H or C.sub.1 -C.sub.6 -alkyl and, in the case where Y=O, R.sup.1 is also --Si(C.sub.1 -C.sub.3 -alkyl).sub.3 or ##STR24## where R.sup.6 =C.sub.1 -C.sub.3 -alkyl, R.sup.2 and R.sup.3 are each, independently of one another, H, C.sub.1 -C.sub.3 -alkyl, --O--R.sup.6, --O-aryl or aryl, where R.sup.6 =C.sub.1 -C.sub.3 -alkyl,
- R.sup.4 and R.sup.5 are each, independently of one another, C.sub.1 -C.sub.20 -alkyl, aryl, C.sub.1 -C.sub.3 -alkyl-aryl, --CO--R.sup.7 or --CO.sub.2 R.sup.7 where R.sup.7 =H or C.sub.1 -C.sub.20 -alkyl, and
- X is Cl, Br, --OSO.sub.3 R.sup.0 where R.sup.0 =C.sub.1 -C.sub.6 -alkyl, aryl, C.sub.1 -C.sub.3 -alkyl-aryl or C.sub.1 -C.sub.3 -alkylene-aryl
- at from -40.degree. to +100.degree. C. to introduce into the primary amine or amino acid a protective group of the formula II ##STR25## where Y and R.sup.2 to R.sup.5 have the abovementioned meanings, into amines or amino acids, and eliminating the protective group after the alkylation reaction.
Dependencies are inferred from the claim text.