Process For Deacetalisation Of Alpha Aminoacetals

A composition comprising at least one N protected α-aminoacetal of formula (II) in the racemic form:

• wherein:
• R1 and R2, are identical or different, and are a linear or branched C1-C12 alkyl group,
• or else R1 and R2 are joined to form a 1,3-dioxolan-2-yl group unsubstituted or substituted on the 4 and/or 5 position(s) by one or more linear or branched C1-C6 alkyl substituents or a 1,3-dioxan-2-yl group unsubstituted or substituted on the 4 and/or 5 and/or 6 position(s) by one or more linear or branched C1-C6 alkyl substituents;
• R3 is a hydrogen;
• a linear or branched C1-C12 alkyl group;
• a C2-C12 alkenyl group;
• a C2-C12 alkynyl group;
• a C3-C10 cycloalkyl group;
• a C3-C10 cycloalkenyl group;
• a cycloalkylalkyl group wherein the cycloalkyl and alkyl groups are defined above;
• a heterocycloalkyl group including 3 to 10 atoms;
• a heterocycloalkylalkyl group wherein the heterocycloalkyl and alkyl groups are defined above;
• a monocyclic, bicyclic or tricyclic C6-C14 aryl group;
• a heteroaryl group including 5 to 14 atoms;
• an arylalkyl group or a heteroarylalkyl group wherein the aryl, heteroaryl and alkyl groups are defined above;
• a C(═O)R4 group wherein R4 is a linear or branched C1-C12 alkyl group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a heterocycloalkyl group, an aryl group or a heteroaryl group as defined above, or R4 is an OR5 group wherein R5 is a hydrogen, a linear or branched C1-C12 alkyl group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a heterocycloalkyl group, an aryl group or a heteroaryl group as defined above, or R4 is an NHR6 group wherein R6 is a hydrogen, a linear or branched C1-C12 alkyl group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a heterocycloalkyl group, an aryl group or a heteroaryl group as defined above;
• all the alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl or heteroarylalkyl radicals above being unsubstituted or substituted;
• and
• P is a group of formula (I)
• wherein:
• R is a hydrogen, a phenyl group or a linear or branched C1-C6 alkyl group, and
• Ar is a phenyl group, a naphthyl group or an anthryl group, optionally substituted by one or more halogen, phenyl, linear or branched C1-C6 alkyl, linear or branched C1-C6 alkoxy, nitro, cyano or methylsulphinyl groups,
• or at least one N-protected α-aminoacetal in the optically active form of formula (R) —(II) or (S)-(II):
• wherein:
• the asterisk * means that the carbon atom is an asymmetric carbon,
• R1, R2 and P are defined above,
• R3 is as defined above, with the exception of H;
• wherein the composition has a pharmacological activity.

A composition comprising at least one N protected α-aminoaldehyde of formula (III) in the racemic form:

• wherein:
• R3 is a hydrogen;
• a linear or branched C1-C12 alkyl group;
• a C2-C12 alkenyl group;
• a C2-C12 alkynyl group;
• a C3-C10 cycloalkyl group;
• a C3-C10 cycloalkenyl group;
• a heterocycloalkyl group including 3 to 10 atoms;
• a heterocycloalkylalkyl group wherein the heterocycloalkyl and alkyl groups are defined above;
• a monocyclic, bicyclic or tricyclic C6-C14 aryl group;
• a heteroaryl group including 5 to 14 atoms;
• an arylalkyl group or a heteroarylalkyl group wherein the aryl, heteroaryl and alkyl groups are as defined above;
• a C(═O)R4 group wherein R4 is a linear or branched C1-C12 alkyl group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a heterocycloalkyl group, an aryl group or a heteroaryl group as defined above, or R4 is an OR5 group wherein R5 is a hydrogen, a linear or branched C1-C12 alkyl group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a heterocycloalkyl group, an aryl group or a heteroaryl group as defined above, or R4 is an NHR6 group wherein R6 is a hydrogen, a linear or branched C1-C12 alkyl group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a heterocycloalkyl group, an aryl group or a heteroaryl group as defined above;
• all the alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl or heteroarylalkyl radicals above being unsubstituted or substituted;
• and
• P is a group of formula (I)
• wherein:
• R is a hydrogen, a phenyl group or a linear or branched C1-C6 alkyl group,
• Ar is a phenyl group, a naphthyl group or an anthryl group, optionally substituted by one or more halogen, phenyl, linear or branched C1-C6 alkyl, linear or branched C1-C6 alkoxy, nitro, cyano or methylsulphinyl groups,
• or at least one N-protected α-aminoaldehyde in the optically active form of formula (R)-(III) or (S)-(III):
• wherein:
• the asterisk * means that the carbon atom is an asymmetric carbon,
• P is defined above,
• R3 is defined above, with the exception of H;
• wherein the composition has a pharmacological activity.

A compound of formula (II), (R) —(II) or (S)-(II):

• wherein which:
• R1 and R2, are identical or different, and are a linear or branched C1-C12 alkyl group;
• R3 is a cycloalkylalkyl group wherein the cycloalkyl group is a C3-C10 cycloalkyl group and the linear or branched alkyl group is a C1-C12 alkyl group;
• P is a benzyloxycarbonyl group, and
• the asterisk * means that the carbon atom is an asymmetric carbon.