2-(4-benzyloxycarbonylamino-1-tert-butoxycarbonylamino-butyl)-thiazole-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: 2-(4-benzyloxycarbonylamino-1-tert-butoxycarbonylamino-butyl)-thiazole-4-carboxylic acid ethyl ester
• CAS No.: 347894-89-7
• Molecular Formula: C₂₃H₃₁N₃O₆S
• Molecular Weight: 477.582
• Mol file: 347894-89-7.mol

Synonyms:2-(4-benzyloxycarbonylamino-1-tert-butoxycarbonylamino-butyl)-thiazole-4-carboxylic acid ethyl ester

Chemical Property of 2-(4-benzyloxycarbonylamino-1-tert-butoxycarbonylamino-butyl)-thiazole-4-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-benzyloxycarbonylamino-1-tert-butoxycarbonylamino-butyl)-thiazole-4-carboxylic acid ethyl ester

There total 7 articles about 2-(4-benzyloxycarbonylamino-1-tert-butoxycarbonylamino-butyl)-thiazole-4-carboxylic acid ethyl 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: 79.0%

ethyl Bromopyruvate (70-23-5) + (4-tert-butoxycarbonylamino-4-thiocarbamoyl-butyl)-carbamic acid benzyl ester (347894-88-6) → 2-(4-benzyloxycarbonylamino-1-tert-butoxycarbonylamino-butyl)-thiazole-4-carboxylic acid ethyl ester (347894-89-7)

Guidance literature:

ethyl Bromopyruvate; (4-tert-butoxycarbonylamino-4-thiocarbamoyl-butyl)-carbamic acid benzyl ester; With potassium hydrogencarbonate; In 1,2-dimethoxyethane; at -15 ℃;

With 2,3,5-trimethyl-pyridine; trifluoroacetic anhydride; In 1,2-dimethoxyethane; at -15 ℃; Further stages.;

DOI:10.1039/b101417j

Reference yield:

L-ornithine (70-26-8,25104-12-5,410523-47-6) → 2-(4-benzyloxycarbonylamino-1-tert-butoxycarbonylamino-butyl)-thiazole-4-carboxylic acid ethyl ester (347894-89-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: CuCO₃ / H₂O / 0.5 h

1.2: NaOH / H₂O / 1 h

1.3: 88 percent / EDTA; aq. HCl / 2 h

2.1: 71 percent / aq. NaOH / tetrahydrofuran / 12 h

3.1: 99 percent / isobutyl chloroformate; N-methylmorpholine; NH₃ / tetrahydrofuran / 1 h / -5 °C

4.1: 99 percent / Lawesson's reagent / tetrahydrofuran / 24 h

5.1: KHCO₃ / 1,2-dimethoxy-ethane / -15 °C

5.2: 79 percent / TFAA; collidine / 1,2-dimethoxy-ethane / -15 °C

With Lawessons reagent; 4-methyl-morpholine; copper(II) carbonate; sodium hydroxide; ammonia; potassium hydrogencarbonate; isobutyl chloroformate; In tetrahydrofuran; 1,2-dimethoxyethane; water; 5.1: Hantzsch thiazole ring forming reaction;

DOI:10.1039/b101417j

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 2-(4-benzyloxycarbonylamino-1-tert-butoxycarbonylamino-butyl)-thiazole-4-carboxylic acid ethyl ester (347894-89-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 71 percent / aq. NaOH / tetrahydrofuran / 12 h

2.1: 99 percent / isobutyl chloroformate; N-methylmorpholine; NH₃ / tetrahydrofuran / 1 h / -5 °C

3.1: 99 percent / Lawesson's reagent / tetrahydrofuran / 24 h

4.1: KHCO₃ / 1,2-dimethoxy-ethane / -15 °C

4.2: 79 percent / TFAA; collidine / 1,2-dimethoxy-ethane / -15 °C

With Lawessons reagent; 4-methyl-morpholine; sodium hydroxide; ammonia; potassium hydrogencarbonate; isobutyl chloroformate; In tetrahydrofuran; 1,2-dimethoxyethane; 4.1: Hantzsch thiazole ring forming reaction;

DOI:10.1039/b101417j

upstream raw materials:

ethyl Bromopyruvate

(4-tert-butoxycarbonylamino-4-thiocarbamoyl-butyl)-carbamic acid benzyl ester

L-ornithine

di-tert-butyl dicarbonate