2-(1-tert-butoxycarbonylamino-ethyl)-6-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-thiazol-2-yl}-nicotinic acid benzyl ester

Base Information

• Chemical Name: 2-(1-tert-butoxycarbonylamino-ethyl)-6-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-thiazol-2-yl}-nicotinic acid benzyl ester
• CAS No.: 348128-79-0
• Molecular Formula: C₃₇H₅₂N₄O₈SSi
• Molecular Weight: 740.993
• Mol file: 348128-79-0.mol

Synonyms:2-(1-tert-butoxycarbonylamino-ethyl)-6-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-thiazol-2-yl}-nicotinic acid benzyl ester

Chemical Property of 2-(1-tert-butoxycarbonylamino-ethyl)-6-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-thiazol-2-yl}-nicotinic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(1-tert-butoxycarbonylamino-ethyl)-6-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-thiazol-2-yl}-nicotinic acid benzyl ester

There total 21 articles about 2-(1-tert-butoxycarbonylamino-ethyl)-6-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-thiazol-2-yl}-nicotinic 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:

3-cyano-6-(dimethoxymethyl)-2-pyridone (156459-19-7) → 2-(1-tert-butoxycarbonylamino-ethyl)-6-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-thiazol-2-yl}-nicotinic acid benzyl ester (348128-79-0)

Guidance literature:

Multi-step reaction with 21 steps

1.1: 6M KOH / ethanol / 8 h / Heating

2.1: 7.73 mg / p-toluenesulfonic acid hydrate / Heating

3.1: 81 percent / DMAP / pyridine / 0.5 h / 0 °C

4.1: Pd(OAc)2; dppp; Et₃N / toluene / 6 h / Heating

5.1: 1.28 g / 70 percent AcOH / tetrahydrofuran / 20 °C

6.1: 94 percent / CaCl₂; NaBH₄ / ethanol / 3.5 h / 0 - 20 °C

7.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 2.5 h / 0 - 20 °C

8.1: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

9.1: 0.42 g / NaN₃ / dimethylformamide / 0.5 h / 20 °C

10.1: H₂ / 10 percent Pd-C / ethanol / 0.5 h / 20 °C

11.1: 1.14 g / Et₃N / CHCl₃ / 4.5 h / 0 - 20 °C

12.1: 2M HCl / tetrahydrofuran / 20 °C

13.1: Et₃N / toluene / 10 h / 0 °C

13.2: 1.91 g / MnO₂ / toluene / 20 °C

14.1: 1M LiOH / H₂O; dioxane / 5 h / 0 - 20 °C

15.1: 83 percent / Et₃N / dimethylformamide / 6 h / 0 - 20 °C

16.1: 77 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

17.1: 83 percent / Jones reagent / acetone / 0.67 h / 0 °C

18.1: K₂CO₃ / H₂O; tetrahydrofuran / 8.5 h / 0 - 20 °C

19.1: 0.47 g / Et₃N; DPPA / dimethylformamide / 0 - 20 °C

20.1: 1M LiOH / tetrahydrofuran; H₂O / 1.5 h / 0 - 20 °C

21.1: 2.03 g / Et₃N / dimethylformamide / 12.5 h / 0 - 20 °C

With hydrogenchloride; dmap; palladium diacetate; potassium hydroxide; lithium hydroxide; sodium tetrahydroborate; sodium azide; jones reagent; diphenyl-phosphinic acid; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1246/bcsj.75.1583

Reference yield:

6-(dimethoxymethyl)-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid (156459-20-0) → 2-(1-tert-butoxycarbonylamino-ethyl)-6-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-thiazol-2-yl}-nicotinic acid benzyl ester (348128-79-0)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 7.73 mg / p-toluenesulfonic acid hydrate / Heating

2.1: 81 percent / DMAP / pyridine / 0.5 h / 0 °C

3.1: Pd(OAc)2; dppp; Et₃N / toluene / 6 h / Heating

4.1: 1.28 g / 70 percent AcOH / tetrahydrofuran / 20 °C

5.1: 94 percent / CaCl₂; NaBH₄ / ethanol / 3.5 h / 0 - 20 °C

6.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 2.5 h / 0 - 20 °C

7.1: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

8.1: 0.42 g / NaN₃ / dimethylformamide / 0.5 h / 20 °C

9.1: H₂ / 10 percent Pd-C / ethanol / 0.5 h / 20 °C

10.1: 1.14 g / Et₃N / CHCl₃ / 4.5 h / 0 - 20 °C

11.1: 2M HCl / tetrahydrofuran / 20 °C

12.1: Et₃N / toluene / 10 h / 0 °C

12.2: 1.91 g / MnO₂ / toluene / 20 °C

13.1: 1M LiOH / H₂O; dioxane / 5 h / 0 - 20 °C

14.1: 83 percent / Et₃N / dimethylformamide / 6 h / 0 - 20 °C

15.1: 77 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

16.1: 83 percent / Jones reagent / acetone / 0.67 h / 0 °C

17.1: K₂CO₃ / H₂O; tetrahydrofuran / 8.5 h / 0 - 20 °C

18.1: 0.47 g / Et₃N; DPPA / dimethylformamide / 0 - 20 °C

19.1: 1M LiOH / tetrahydrofuran; H₂O / 1.5 h / 0 - 20 °C

20.1: 2.03 g / Et₃N / dimethylformamide / 12.5 h / 0 - 20 °C

With hydrogenchloride; dmap; palladium diacetate; lithium hydroxide; sodium tetrahydroborate; sodium azide; jones reagent; diphenyl-phosphinic acid; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1246/bcsj.75.1583

Reference yield:

methyl 6-dimethoxymethyl-2-oxo-1,2-dihydropyridine-3-carboxylate (348128-54-1) → 2-(1-tert-butoxycarbonylamino-ethyl)-6-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-thiazol-2-yl}-nicotinic acid benzyl ester (348128-79-0)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 81 percent / DMAP / pyridine / 0.5 h / 0 °C

2.1: Pd(OAc)2; dppp; Et₃N / toluene / 6 h / Heating

3.1: 1.28 g / 70 percent AcOH / tetrahydrofuran / 20 °C

4.1: 94 percent / CaCl₂; NaBH₄ / ethanol / 3.5 h / 0 - 20 °C

5.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 2.5 h / 0 - 20 °C

6.1: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

7.1: 0.42 g / NaN₃ / dimethylformamide / 0.5 h / 20 °C

8.1: H₂ / 10 percent Pd-C / ethanol / 0.5 h / 20 °C

9.1: 1.14 g / Et₃N / CHCl₃ / 4.5 h / 0 - 20 °C

10.1: 2M HCl / tetrahydrofuran / 20 °C

11.1: Et₃N / toluene / 10 h / 0 °C

11.2: 1.91 g / MnO₂ / toluene / 20 °C

12.1: 1M LiOH / H₂O; dioxane / 5 h / 0 - 20 °C

13.1: 83 percent / Et₃N / dimethylformamide / 6 h / 0 - 20 °C

14.1: 77 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

15.1: 83 percent / Jones reagent / acetone / 0.67 h / 0 °C

16.1: K₂CO₃ / H₂O; tetrahydrofuran / 8.5 h / 0 - 20 °C

17.1: 0.47 g / Et₃N; DPPA / dimethylformamide / 0 - 20 °C

18.1: 1M LiOH / tetrahydrofuran; H₂O / 1.5 h / 0 - 20 °C

19.1: 2.03 g / Et₃N / dimethylformamide / 12.5 h / 0 - 20 °C

With hydrogenchloride; dmap; palladium diacetate; lithium hydroxide; sodium tetrahydroborate; sodium azide; jones reagent; diphenyl-phosphinic acid; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; acetic acid; triethylamine; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1246/bcsj.75.1583

upstream raw materials:

benzyl bromide

2-(1-tert-butoxycarbonylamino-ethyl)-6-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-thiazol-2-yl}-nicotinic acid

3-cyano-6-(dimethoxymethyl)-2-pyridone

6-(dimethoxymethyl)-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid

Downstream raw materials:

(R)-2'-[5-Benzyloxycarbonyl-6-((R)-1-tert-butoxycarbonylamino-ethyl)-pyridin-2-yl]-4,5-dihydro-[2,4']bithiazolyl-4-carboxylic acid

t-butyl (4S)-2-(2-{3-benzyloxycarbonyl-2-[(1S)-1-t-butoxycarbonylaminoethyl]pyridin-6-yl}-1,3-thiazol-4-yl)-4,5-dihydro-1,3-thiazole-4-carboxylate

t-butyl (4S)-2-(2-{3-benzyloxycarbonyl-2-[(1R)-1-t-butoxycarbonylaminoethyl]pyridin-6-yl}-1,3-thiazol-4-yl)-4,5-dihydro-1,3-thiazole-4-carboxylate

2-(1-tert-butoxycarbonylamino-ethyl)-6-[4-(1-tert-butoxycarbonyl-2-hydroxy-ethylthiocarbamoyl)-thiazol-2-yl]-nicotinic acid benzyl ester

Refernces

• 1、 Okabe, Akihiro,Ito, Akinori,Okumura, Kazuo,Shin, Chung-Gi. "Convenient synthesis of a central 2,3,6-trisubstituted pyridine skeleton of a macrobicyclic antibiotic, cyclothiazomycin". . p. 380 - 381. Retrieved 2007/10/03.