methyl (2S)-2,6-diaminohexanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 0.4%(w/w) solution of HA in water was prepared. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid. To each 100 ml of this solution was added 0.76 g of EDC with stirring until the EDC had completely dissolved. To each 100 ml of the HA/EDC solution was added 0.20 g of lysine methyl ester (LME) with stirring until the LME had completely dissolved. The addition of HA, EDC, and LME was conducted at room temperature; once the final HA/EDC/LME solution had been formed, it was stored at 4° C. until needed. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid had completely dissolved had completely dissolved was conducted at room temperature

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 0.4%(w/w) solution of HA in water was prepared. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid. To each 100 ml of this solution was added 0.76 g of EDC with stirring until the EDC had completely dissolved. To each 100 ml of the HA/EDC solution was added 0.20 g of lysine methyl ester (LME) with stirring until the LME had completely dissolved. The addition of HA, EDC, and LME was conducted at room temperature; once the final HA/EDC/LME solution had been formed, it was stored at 4° C. until needed. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid had completely dissolved had completely dissolved was conducted at room temperature

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 0.4%(w/w) solution of HA in water was prepared. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid. To each 100 ml of this solution was added 0.76 g of EDC with stirring until the EDC had completely dissolved. To each 100 ml of the HA/EDC solution was added 0.20 g of lysine methyl ester (LME) with stirring until the LME had completely dissolved. The addition of HA, EDC, and LME was conducted at room temperature; once the final HA/EDC/LME solution had been formed, it was stored at 4° C. until needed. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid had completely dissolved had completely dissolved was conducted at room temperature

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 0.4%(w/w) solution of HA in water was prepared. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid. To each 100 ml of this solution was added 0.76 g of EDC with stirring until the EDC had completely dissolved. To each 100 ml of the HA/EDC solution was added 0.20 g of lysine methyl ester (LME) with stirring until the LME had completely dissolved. The addition of HA, EDC, and LME was conducted at room temperature; once the final HA/EDC/LME solution had been formed, it was stored at 4° C. until needed. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid had completely dissolved had completely dissolved was conducted at room temperature

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 0.4%(w/w) solution of HA in water was prepared. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid. To each 100 ml of this solution was added 0.76 g of EDC with stirring until the EDC had completely dissolved. To each 100 ml of the HA/EDC solution was added 0.20 g of lysine methyl ester (LME) with stirring until the LME had completely dissolved. The addition of HA, EDC, and LME was conducted at room temperature; once the final HA/EDC/LME solution had been formed, it was stored at 4° C. until needed. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid had completely dissolved had completely dissolved was conducted at room temperature

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 0.4% (w/w) solution of HA in water was prepared. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid. To each 100 ml of this solution was added 0.76 g of EDC with stirring until the EDC had completely dissolved. To each 100 ml of the HA/EDC solution was added 0.20 g of lysine methyl ester (LME) with stirring until the LME had completely dissolved. The addition of HA, EDC, and LME was conducted at room temperature; once the final HA/EDC/LME solution had been formed, it was stored at 4° C. until needed. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid had completely dissolved had completely dissolved was conducted at room temperature

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 0.4%(w/w) solution of HA in water was prepared. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid. To each 100 ml of this solution was added 0.76 g of EDC with stirring until the EDC had completely dissolved. To each 100 ml of the HA/EDC solution was added 0.20 g of lysine methyl ester (LME) with stirring until the LME had completely dissolved. The addition of HA, EDC, and LME was conducted at room temperature; once the final HA/EDC/LME solution had been formed, it was stored at 4° C. until needed. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid had completely dissolved had completely dissolved was conducted at room temperature

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 0.4%(w/w) solution of HA in water was prepared. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid. To each 100 ml of this solution was added 0.76 g of EDC with stirring until the EDC had completely dissolved. To each 100 ml of the HA/EDC solution was added 0.20 g of lysine methyl ester (LME) with stirring until the LME had completely dissolved. The addition of HA, EDC, and LME was conducted at room temperature; once the final HA/EDC/LME solution had been formed, it was stored at 4° C. until needed. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid had completely dissolved had completely dissolved was conducted at room temperature

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 0.4%(w/w) solution of HA in water was prepared. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid. To each 100 ml of this solution was added 0.76 g of EDC with stirring until the EDC had completely dissolved. To each 100 ml of the HA/EDC solution was added 0.20 g of lysine methyl ester (LME) with stirring until the LME had completely dissolved. The addition of HA, EDC, and LME was conducted at room temperature; once the final HA/EDC/LME solution had been formed, it was stored at 4° C. until needed. The pH of this solution was adjusted to between 4.3 and 4.75 by addition of acid had completely dissolved had completely dissolved was conducted at room temperature

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Nα-tert-Butyloxycarbonyl-lysine was reacted with trimethylsilyldiazomethan in ethanol. The resulting methyl ester amine was transformed to the Nε-methyl derivative via benzaldehyde and sodium borohydride, formaldehyde and sodium boronhydride and hydrogenolysis (Andruszkiewicz, J. Pol. Chem. 1988, 62, 257) followed by N-alkylation with 2-(pinacolborono)benzyl bromide. The resulting Nα-tert-butyloxycarbonyl, Nε-methyl, Nε-(2-pinacolboronobenzyl) methyl lysinate was treated with methanol and trimethylsilyl chloride, 10:1, to give Nε-methyl, Nε-(2-boronobenzyl), methyl lysinate, dihydrochloride:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Nα-tert-Butyloxycarbonyl-lysine was reacted with trimethylsilyldiazomethan in ethanol. The resulting methyl ester amine was transformed to the Nε-methyl derivative via benzaldehyde and sodium borohydride, formaldehyde and sodium boronhydride and hydrogenolysis (Andruszkiewicz, J. Pol. Chem. 1988, 62, 257) followed by N-alkylation with 2-(pinacolborono)benzyl bromide. The resulting Nα-tert-butyloxycarbonyl, Nε-methyl, Nε-(2-pinacolboronobenzyl) methyl lysinate was treated with methanol and trimethylsilyl chloride, 10:1, to give Nε-methyl, Nε-(2-boronobenzyl), methyl lysinate, dihydrochloride:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Nα-tert-Butyloxycarbonyl-lysine was reacted with trimethylsilyldiazomethan in ethanol. The resulting methyl ester amine was transformed to the Nε-methyl derivative via benzaldehyde and sodium borohydride, formaldehyde and sodium boronhydride and hydrogenolysis (Andruszkiewicz, J. Pol. Chem. 1988, 62, 257) followed by N-alkylation with 2-(pinacolborono)benzyl bromide. The resulting Nα-tert-butyloxycarbonyl, Nε-methyl, Nε-(2-pinacolboronobenzyl) methyl lysinate was treated with methanol and trimethylsilyl chloride, 10:1, to give Nε-methyl, Nε-(2-boronobenzyl), methyl lysinate, dihydrochloride: