(2S)-methyl-[2-tert-butoxycarbonylamino-4-oxo-4-(3,4,5-trimethoxyphenyl)]butanoate

Base Information

• Chemical Name: (2S)-methyl-[2-tert-butoxycarbonylamino-4-oxo-4-(3,4,5-trimethoxyphenyl)]butanoate
• CAS No.: 327025-09-2
• Molecular Formula: C₁₉H₂₇NO₈
• Molecular Weight: 397.425
• Mol file: 327025-09-2.mol

Synonyms:(2S)-methyl-[2-tert-butoxycarbonylamino-4-oxo-4-(3,4,5-trimethoxyphenyl)]butanoate

Chemical Property of (2S)-methyl-[2-tert-butoxycarbonylamino-4-oxo-4-(3,4,5-trimethoxyphenyl)]butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-methyl-[2-tert-butoxycarbonylamino-4-oxo-4-(3,4,5-trimethoxyphenyl)]butanoate

There total 1 articles about (2S)-methyl-[2-tert-butoxycarbonylamino-4-oxo-4-(3,4,5-trimethoxyphenyl)]butanoate 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: 31.0%

3,4,5-Trimethoxybenzoyl chloride (4521-61-3) + N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester (93267-04-0,170848-34-7,889670-02-4) → (2S)-methyl-[2-tert-butoxycarbonylamino-4-oxo-4-(3,4,5-trimethoxyphenyl)]butanoate (327025-09-2)

Guidance literature:

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester; With zinc copper; In N,N-dimethyl acetamide; benzene; at 20 ℃; for 3h; sonication;

3,4,5-Trimethoxybenzoyl chloride; With bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl acetamide; benzene; for 2h; sonication;

DOI:10.1016/S0040-4020(00)00862-0

Reference yield: 91.0%

(2S)-methyl-[2-tert-butoxycarbonylamino-4-oxo-4-(3,4,5-trimethoxyphenyl)]butanoate (327025-09-2) → (2S)-methyl-[2-tert-butoxycarbonylamino-4-(3,4,5-trimethoxyphenyl)]butanoate (327025-10-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; water; for 22h; under 3102.89 Torr;

DOI:10.1016/S0040-4020(00)00862-0

Reference yield:

(2S)-methyl-[2-tert-butoxycarbonylamino-4-oxo-4-(3,4,5-trimethoxyphenyl)]butanoate (327025-09-2) → colchicine (64-86-8,54192-66-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 91 percent / H₂ / Pd/C / ethanol; H₂O / 22 h / 3102.89 Torr

2.1: 93 percent / NaHCO₃; silver trifluoroacetate; I₂ / CHCl₃ / 2 h / 0 °C

3.1: trifluoroacetic acid / diethyl ether / 3 h / 20 °C

4.1: 454 mg / 4-(dimethylamino)pyridine; Et₃N / diethyl ether / 10 h

5.1: 60 percent / Et₂NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 15 h / 90 °C

6.1: 91 percent / potassium carbonate / methanol / 11 h / 20 °C

7.1: 100 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

8.1: potassium carbonate / methanol / 1 h / Heating

8.2: 64 percent / KOH / methanol / 3 h / Heating

9.1: 70 percent / various solvent(s) / 40 h / Heating

10.1: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / 35 °C

11.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h

12.1: 45 percent Turnov_. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C

13.1: 62 percent / Et₃N; trimethylsilyl triflate / CH₂Cl₂ / 2 h / 0 °C

14.1: HCl / diethyl ether / 1 h / 20 °C

14.2: 98 percent / 4-(dimethylamino)pyridine; Et₃N / diethyl ether / 10 h / 25 °C

With hydrogenchloride; dmap; bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; copper(l) iodide; trimethylsilyl trifluoromethanesulfonate; hydrogen; iodine; silver trifluoroacetate; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; diethylamine; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; water; dimethyl sulfoxide; 5.1: Sonogashira coupling / 9.1: intramolecular Diels-Alder reaction;

DOI:10.1016/S0040-4020(00)00862-0

upstream raw materials:

3,4,5-Trimethoxybenzoyl chloride

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

Downstream raw materials:

(2S)-methyl-[2-tert-butoxycarbonylamino-4-(3,4,5-trimethoxyphenyl)]butanoate

colchicine

(2S)-methyl-[2-tert-butoxycarbonylamino-4-(2-iodo-3,4,5-trimethoxyphenyl)]butanoate

(2S)-methyl-[2-acetamido-4-(2-trimethylsilylethynyl-3,4,5-trimethoxyphenyl)]butanoate

Refernces