N-carbobenzoxy-N-chloroglycine methyl ester

Base Information

• Chemical Name: N-carbobenzoxy-N-chloroglycine methyl ester
• CAS No.: 129778-98-9
• Molecular Formula: C₁₁H₁₂ClNO₄
• Molecular Weight: 257.674

Synonyms:N-carbobenzoxy-N-chloroglycine methyl ester

Chemical Property of N-carbobenzoxy-N-chloroglycine methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of N-carbobenzoxy-N-chloroglycine methyl ester

There total 1 articles about N-carbobenzoxy-N-chloroglycine methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methyl N-benzyloxycarbonylglycinate (1212-53-9) → N-carbobenzoxy-N-chloroglycine methyl ester (129778-98-9)

Guidance literature:

With tert-butylhypochlorite; In methanol; at 0 ℃; for 17h;

DOI:10.1080/00397919608003521

Reference yield: 96.0%

methanol (67-56-1) + N-carbobenzoxy-N-chloroglycine methyl ester (129778-98-9) → methyl 2-(benzyloxycarbonylamino)-2-methoxyacetate (127357-37-3,58237-86-8)

Guidance literature:

With sodium methylate; at -78 ℃; for 6h;

DOI:10.1080/00397919608003521

Reference yield: 95.0%

N-carbobenzoxy-N-chloroglycine methyl ester (129778-98-9) → methyl N-benzyloxycarbonylglycinate (1212-53-9)

Guidance literature:

With triethylamine; at -78 ℃; further bases;

DOI:10.1080/00397919608003521

upstream raw materials:

methyl N-benzyloxycarbonylglycinate

Downstream raw materials:

methyl 2-(benzyloxycarbonylamino)-2-methoxyacetate

N-carbobenzoxy-α-propoxyglycine propyl ester

N-carbobenzoxy-α-ethoxyglycine ethyl ester

N-carbobenzoxy-α-isobutoxyglycine isobutyl ester

Refernces

Preparation of protected α-alkoxyglycines

10.1080/00397919608003521

The research details the synthesis of N-Carbobenzoxy-protected α-alkoxyglycines, which are unnatural amino acids with an electronegative oxygen atom directly attached to the α-carbon atom. The purpose of this study was to develop methods for synthesizing these compounds to enable the creation of peptide analogs containing p-oxa analogs of α-amino acids. The researchers used a two-pronged approach: one involving the H2SO4-catalyzed O-alkylation of N-carbobenzoxy-α-hydroxyglycine and another through base treatment of N-carbobenzoxy-N-chloroglycine methyl ester in the corresponding alcohol. The synthesis yielded various α-alkoxyglycine esters, which upon saponification, gave free acids suitable for peptide synthesis.

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