(S)-2-(Bis-tert-butoxycarbonylmethyl-amino)-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-2-(Bis-tert-butoxycarbonylmethyl-amino)-propionic acid benzyl ester
• CAS No.: 171557-06-5
• Molecular Formula: C₂₂H₃₃NO₆
• Molecular Weight: 407.507
• Mol file: 171557-06-5.mol

Synonyms:(S)-2-(Bis-tert-butoxycarbonylmethyl-amino)-propionic acid benzyl ester

Chemical Property of (S)-2-(Bis-tert-butoxycarbonylmethyl-amino)-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of (S)-2-(Bis-tert-butoxycarbonylmethyl-amino)-propionic acid benzyl ester

There total 1 articles about (S)-2-(Bis-tert-butoxycarbonylmethyl-amino)-propionic acid benzyl 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: 75.0%

L-alanine benzyl ester p-toluenesulfonate (42854-62-6) + t-butyl iodoacetate (49827-15-8) → (S)-2-(Bis-tert-butoxycarbonylmethyl-amino)-propionic acid benzyl ester (171557-06-5)

Guidance literature:

With pH 7.0 phosphate buffer; In dimethyl sulfoxide; for 48h;

DOI:10.1021/jo00126a059

Reference yield:

(S)-2-(Bis-tert-butoxycarbonylmethyl-amino)-propionic acid benzyl ester (171557-06-5) → {Bis-[(S)-2-(bis-carboxymethyl-amino)-propyl]-amino}-acetic acid; hydrochloride

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / H₂ / 5percent Pd/C / methanol / 32 h / 760 Torr

2: 1.) N-methylmorpholine, isobutyl chloroformate, 2.) N-methylmorpholine / 1.) THF, -25 deg C, 10 min, 2.) THF, -30 to -25 deg C, 5 h

3: 57 percent / BH₃*THF / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) reflux, 1 h

4: 98 percent / 12 M HCl / dioxane / 1 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; borane-THF; hydrogen; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1021/jo00126a059

upstream raw materials:

L-alanine benzyl ester p-toluenesulfonate

t-butyl iodoacetate