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ChemicalBook CAS DataBase List METHYL 6-AMINOCAPROATE HYDROCHLORIDE
1926-80-3

METHYL 6-AMINOCAPROATE HYDROCHLORIDE synthesis

5synthesis methods
Methanol

67-56-1

6-Aminocaproic acid

60-32-2

METHYL 6-AMINOCAPROATE HYDROCHLORIDE

1926-80-3

Thionyl chloride (1.4 eq.) was slowly added dropwise to a methanolic suspension of 6-aminohexanoic acid (1 eq.) at 0 °C while maintaining stirring. The reaction mixture was continued to be stirred overnight at room temperature. Subsequently, the solvent and unreacted thionyl chloride were removed by distillation under reduced pressure to give methyl 6-aminohexanoate hydrochloride.

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Yield:1926-80-3 99%

Reaction Conditions:

with hydrogen chloride (gas) in methanol

Steps:

XV.1 Synthesis of DOTA-Biotin conjugates
1. Preparation of methyl 6-aminocaproate hydrochloride. Hydrogen chloride (gas) was added to a solution of 20.0 g (152 mmol) of 6-aminocaproic acid in 250 ml of methanol via rapid bubbling for 2-3 minutes. The mixture was stirred at 15-25° C. for 3 hours and then concentrated to afford 27.5 g of the product as a white solid (99%): H-NMR (DMSO) 9.35 (1 H, broad t), 3.57 (3H, s), 3.14 (2H, quartet), 2.28 (2H, t), 1.48 (4H, multiplet), and 1.23 ppm (2H, multiplet).

References:

NeoRx Corporation US6022966, 2000, A

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