2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carboxamide

Base Information

• Chemical Name: 2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carboxamide
• CAS No.: 182120-82-7
• Molecular Formula: C₁₀H₁₅N₃O₃S
• Molecular Weight: 257.313
• Mol file: 182120-82-7.mol

Synonyms:2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carboxamide

Chemical Property of 2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carboxamide

There total 1 articles about 2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carboxamide 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:

N-(tert-butoxycarbonyl)glycine methyl ester (31954-27-5) → 2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carboxamide (182120-82-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ammonium hydroxide / methanol / 6 h / Inert atmosphere; Sonication

2.1: Lawessons reagent / tetrahydrofuran / 20 °C / Inert atmosphere; Sealed tube

3.1: potassium hydrogencarbonate / 1,2-dimethoxyethane / 0.25 h / 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: ammonium hydroxide / methanol / 20 °C / Inert atmosphere; Sonication

With Lawessons reagent; ammonium hydroxide; potassium hydrogencarbonate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; 3.1: |Hantzsch Thiazole Synthesis / 3.2: |Hantzsch Thiazole Synthesis;

DOI:10.1021/acsmedchemlett.6b00488

Reference yield:

2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carboxamide (182120-82-7) → largazole (1009815-87-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 0 °C

2.1: sodium hydrogencarbonate / methanol / 2 h / 70 °C / pH 6 / aq. phosphate buffer

3.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C

3.2: 0 - 20 °C

4.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C

5.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane; acetonitrile

6.1: triethylsilane; trifluoroacetic anhydride / 2 h / 0 - 20 °C

7.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C

With triethylsilane; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium hydrogencarbonate; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; trifluoroacetic anhydride; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/j.bmc.2011.02.024

Reference yield:

2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carboxamide (182120-82-7) → ((R)-1-{(S)-2-[(4-Carbamimidoyl-thiazol-2-ylmethyl)-carbamoyl]-pyrrolidine-1-carbonyl}-2,2-diphenyl-ethylamino)-acetic acid tert-butyl ester; compound with acetic acid

Guidance literature:

Multi-step reaction with 7 steps

1: (CF₃CO)2O; Et₃N / CH₂Cl₂

2: HCl / ethyl acetate

3: EDC; HOBT; Et₃N / dimethylformamide / 20 °C

4: HCl / ethyl acetate / 20 °C

5: iPr₂NEt / acetonitrile / 20 °C

6: aq. NH₂OH*HCl; Na₂CO₃ / ethanol / Heating

7: H₂ / Pd/C / methanol

With hydrogenchloride; hydroxylamine hydrochloride; hydrogen; sodium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; palladium on activated charcoal; In methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm030025j

upstream raw materials:

N-(tert-butoxycarbonyl)glycine methyl ester

Downstream raw materials:

(S)-1-((R)-2-Amino-3,3-diphenyl-propionyl)-pyrrolidine-2-carboxylic acid (4-cyano-thiazol-2-ylmethyl)-amide

largazole

(S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((R)-2'-(((tert-butoxycarbonyl)amino)methyl)-4-methyl-4,5-dihydro[2,4'-bithiazole]-4-carboxamido)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate

(5R,8S,11S)-8-isopropyl-5-methyl-11-((E)-4-(tritylthio)but-1-en-1-yl)-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1⁽¹⁸⁾,2⁽²⁰⁾,16⁽¹⁹⁾-triene-6,9,13-trione