methyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate

Base Information

• Chemical Name: methyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate
• CAS No.: 348128-71-2
• Molecular Formula: C₃₄H₄₁N₃O₅SSi
• Molecular Weight: 631.868
• Mol file: 348128-71-2.mol

Synonyms:methyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate

Chemical Property of methyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate

There total 13 articles about methyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate 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) → methyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate (348128-71-2)

Guidance literature:

Multi-step reaction with 13 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

With hydrogenchloride; dmap; palladium diacetate; potassium hydroxide; sodium tetrahydroborate; sodium azide; 1,3-bis-(diphenylphosphino)propane; hydrogen; toluene-4-sulfonic acid; acetic acid; triethylamine; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1246/bcsj.75.1583

Reference yield:

6-(dimethoxymethyl)-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid (156459-20-0) → methyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate (348128-71-2)

Guidance literature:

Multi-step reaction with 12 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

With hydrogenchloride; dmap; palladium diacetate; sodium tetrahydroborate; sodium azide; 1,3-bis-(diphenylphosphino)propane; hydrogen; toluene-4-sulfonic acid; acetic acid; triethylamine; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1246/bcsj.75.1583

Reference yield:

methyl 6-dimethoxymethyl-2-oxo-1,2-dihydropyridine-3-carboxylate (348128-54-1) → methyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate (348128-71-2)

Guidance literature:

Multi-step reaction with 11 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

With hydrogenchloride; dmap; palladium diacetate; sodium tetrahydroborate; sodium azide; 1,3-bis-(diphenylphosphino)propane; hydrogen; acetic acid; triethylamine; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1246/bcsj.75.1583

upstream raw materials:

L-cysteine methyl ester hydrochloride

{1-[3-(tert-butyl-diphenyl-silanyloxymethyl)-6-formyl-pyridin-2-yl]-ethyl}-carbamic acid tert-butyl ester

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

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

Downstream raw materials:

phenacyl (RS)-2-(1H-2-t-butoxycarbonyl-1-oxo-2,3-dihydropyrrolo[3,4-b]pyridin-5-yl)-1,3-thiazole-4-carboxylate

phenacyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(hydroxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate

(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