N-[2-(Boc-amino)ethyl]glycine ethyl ester hydrochloride
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N-[2-(Boc-amino)ethyl]glycine ethyl ester hydrochloride

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Category
DL-Amino Acids
Catalog number
BAT-000437
CAS number
347890-34-0
Molecular Formula
C11H22N2O4·HCl
Molecular Weight
282.76
N-[2-(Boc-amino)ethyl]glycine ethyl ester hydrochloride
IUPAC Name
ethyl 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylamino]acetate;hydrochloride
Synonyms
N-(Boc-aminoethyl)-Gly-OEt HCl; Ethyl [2-(Boc-amino)ethylamino]acetate hydrochloride; Ethyl N-[(2-Boc-amino)ethyl]glycinate hydrochloride
Related CAS
72648-80-7 (free base)
Appearance
White solid
Purity
≥ 97% (NMR)
Melting Point
116-119 °C
Boiling Point
352ºC at 760mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H22N2O4.ClH/c1-5-16-9(14)8-12-6-7-13-10(15)17-11(2,3)4;/h12H,5-8H2,1-4H3,(H,13,15);1H
InChI Key
CZTZMHQGYIOSNM-UHFFFAOYSA-N
Canonical SMILES
CCOC(=O)CNCCNC(=O)OC(C)(C)C.Cl
1.A convenient and scalable synthesis of ethyl N-[(2-Boc-amino)ethyl]glycinate and its hydrochloride. Key intermediates for peptide nucleic acid synthesis.
Viirre RD1, Hudson RH. J Org Chem. 2003 Feb 21;68(4):1630-2.
An improved synthesis of ethyl N-[(2-Boc-amino)ethyl]glycinate and its hydrochloride salt is reported. The synthesis is based on the reductive alkylation of Boc-ethylenediamine with ethyl glyoxylate hydrate and furnishes the title compound in near quantitative yield and high purity without chromatography. This compound is suitable, as is, for the synthesis peptide nucleic acid monomers. Further, conversion to the hydrochloride salt provides a stable, nonhygroscopic solid that is a convenient form for handling and storage.
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