150094-69-2

Upstream product

• 312-84-5 D-Serine 
• 76-83-5 trityl chloride 

Downstream Products

• 503564-99-6 (R)-allyl 3-hydroxy-2-(tritylamino)propanoate 
• 1159573-87-1 O-methyl-N-trityl-D-serine 
• 1085337-40-1 N-trityl-D-serine (o-allylbenzyl)amide 
• 503565-00-2 N-triphenylmethyl-(R)-serine(O-methanesulfonyl) allyl ester 
• 503565-02-4 (2S,6R)-N²-triphenylmethyl-N⁶-(9H-fluorenylmethoxycarbonyl)-lanthionine O¹-allyl-O⁷-tert-butyl ester 
• 503565-01-3 N-triphenylmethyl-β-iodo-(S)-alanine allyl ester 
• 618097-75-9 (R)-1-triphenylmethylaziridine-2-carboxylic acid allyl ester 
• 1159573-88-2 N-benzyl-O-methyl-N₂-trityl-D-serinamide 

Relevant academic research and scientific papers

Synthesis of orthogonally protected lanthionines: A reassessment of the use of alanyl β-cation equivalents

Whilst developing a strategy for the solid-phase synthesis of lanthionine-containing peptides, we became aware of some problems with a previously published route for the synthesis of orthogonally-protected lanthionine. We report a structural reassignment

Orthogonally protected lanthionines: Synthesis and use for the solid-phase synthesis of an analogue of nisin ring C

(Chemical Equation Presented) Lanthionine, a thioether analogue of cystine, is a key component of the lantibiotics, a family of modified peptides bearing multiple thioether bridges resulting from posttranslational modifications between side chains. It is also used as a conformational constraint in medicinally active peptides. We have explored two synthetic routes to give lanthionine, orthogonally protected with Alloc/allyl and Fmoc groups. One route utilized a carbamate-protected iodoalanine that yielded a mixture of diastereoisomers, and one utilized a trityl-protected iodoalanine, formed via a Mitsunobu reaction, that gave the single desired lanthionine, in complete regio-and diastereoselectivity. We then used this orthogonally protected lanthionine in the solid-phase synthesis of an analogue of a fragment of nisin containing its ring C. The chemoselective deprotection of the allyl and Alloc groups of the incorporated lanthionine unit was followed by regio- and stereoselective cyclization on resin to give the desired lanthionine-bridged peptide.

Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates

Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para- methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.

Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates

Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para-methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.

PROCESSES FOR PREPARATION OF POLYMORPHIC FORMS OF LACOSAMIDE

The present invention relates to processes for the preparation of crystalline polymorphic forms of lacosamide (Formula I), including processes for inter-conversion among such polymorphic forms.

PROCESSES FOR REDUCING IMPURITIES IN LACOSAMIDE

The present invention relates to processes for reducing impurities in lacosamide during the preparation of lacosamide. The invention provides processes for minimizing or removing impurities such as (2R)-2-(acetylamino)-3-(benzylamino)-3-oxopropyl acetate of Formula II or (2R)-2-propanoylamino-N-benzyl-3-methoxypropionamide of Formula III in lacosamide.

Intermediate compounds and their use in preparation of lacosamide

The present invention is concerned with novel compounds and their use for the preparation of lacosamide. The present invention also contemplates processes for the preparation of lacosamide employing the novel compound of general Formula II, Formula IIa or Formula IIb as intermediate. Wherein R1 is -OH or -OMe; R2 is -OH or -NH-CH2-C6H5.

INTERMEDIATE COMPOUNDS AND THEIR USE IN PREPARATION OF LACOSAMIDE

The present invention is concerned with novel compounds and their use for the preparation of lacosamide. The present invention also contemplates processes for the preparation of lacosamide employing the novel compound of general Formula II, Formula IIa or Formula IIb as intermediate. Wherein R1 is —OH or —OMe;R2 is —OH or —NH—CH2—C6H5.

Synthesis of orthogonally protected lanthionines

Synthetic approaches to the lantibiotics, a family of thioether-bridged antimicrobial peptides, require flexible synthetic routes to a variety of orthogonally protected derivatives of lanthionine 1. The most direct approaches to lanthionine involve the re