6-[1-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propionylamino)-2-hydroxy-ethyl]-5-(4-ethoxycarbonyl-thiazol-2-yl)-pyridine-2-carboxylic acid ethyl ester

Base Information

• Chemical Name: 6-[1-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propionylamino)-2-hydroxy-ethyl]-5-(4-ethoxycarbonyl-thiazol-2-yl)-pyridine-2-carboxylic acid ethyl ester
• CAS No.: 200482-35-5
• Molecular Formula: C₂₇H₃₀N₄O₉S
• Molecular Weight: 586.623
• Mol file: 200482-35-5.mol

Synonyms:

Chemical Property of 6-[1-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propionylamino)-2-hydroxy-ethyl]-5-(4-ethoxycarbonyl-thiazol-2-yl)-pyridine-2-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[1-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propionylamino)-2-hydroxy-ethyl]-5-(4-ethoxycarbonyl-thiazol-2-yl)-pyridine-2-carboxylic acid ethyl ester

There total 13 articles about 6-[1-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propionylamino)-2-hydroxy-ethyl]-5-(4-ethoxycarbonyl-thiazol-2-yl)-pyridine-2-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:

ethyl 2-(pyridin-3-yl) thiazole-4-carboxylate (39067-28-2) → 6-[1-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propionylamino)-2-hydroxy-ethyl]-5-(4-ethoxycarbonyl-thiazol-2-yl)-pyridine-2-carboxylic acid ethyl ester (200482-35-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 94 percent / m-CPBA / CH₂Cl₂

2: 62 percent / Et₃N / acetonitrile

3: NaOH / H₂O; methanol

4: dimethylformamide

5: 1.) m-CPBA, 2.) Ac₂O, 3.) NaOEt / 1.) CH₂Cl₂

6: Et₃N, DMAP / CH₂Cl₂

7: LiCl, Pd(Ph₃P)4 / tetrahydrofuran

8: 75 percent / KMnO₄, MgSO₄ / H₂O

9: Et₃N, DMAP / CH₂Cl₂

10: DMAP / CH₂Cl₂

11: NaN₃ / dimethylformamide

12: H₂ / Pd/C / ethanol

13: AcOH / H₂O

14: BOP / acetonitrile

With dmap; sodium hydroxide; potassium permanganate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; hydrogen; sodium ethanolate; acetic anhydride; magnesium sulfate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1246/cl.1997.1203

Reference yield:

2-(1-Oxy-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester (200482-27-5) → 6-[1-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propionylamino)-2-hydroxy-ethyl]-5-(4-ethoxycarbonyl-thiazol-2-yl)-pyridine-2-carboxylic acid ethyl ester (200482-35-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 62 percent / Et₃N / acetonitrile

2: NaOH / H₂O; methanol

3: dimethylformamide

4: 1.) m-CPBA, 2.) Ac₂O, 3.) NaOEt / 1.) CH₂Cl₂

5: Et₃N, DMAP / CH₂Cl₂

6: LiCl, Pd(Ph₃P)4 / tetrahydrofuran

7: 75 percent / KMnO₄, MgSO₄ / H₂O

8: Et₃N, DMAP / CH₂Cl₂

9: DMAP / CH₂Cl₂

10: NaN₃ / dimethylformamide

11: H₂ / Pd/C / ethanol

12: AcOH / H₂O

13: BOP / acetonitrile

With dmap; sodium hydroxide; potassium permanganate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; hydrogen; sodium ethanolate; acetic anhydride; magnesium sulfate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1246/cl.1997.1203

Reference yield:

2-(6-Cyano-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester (200482-28-6) → 6-[1-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propionylamino)-2-hydroxy-ethyl]-5-(4-ethoxycarbonyl-thiazol-2-yl)-pyridine-2-carboxylic acid ethyl ester (200482-35-5)

Guidance literature:

Multi-step reaction with 12 steps

1: NaOH / H₂O; methanol

2: dimethylformamide

3: 1.) m-CPBA, 2.) Ac₂O, 3.) NaOEt / 1.) CH₂Cl₂

4: Et₃N, DMAP / CH₂Cl₂

5: LiCl, Pd(Ph₃P)4 / tetrahydrofuran

6: 75 percent / KMnO₄, MgSO₄ / H₂O

7: Et₃N, DMAP / CH₂Cl₂

8: DMAP / CH₂Cl₂

9: NaN₃ / dimethylformamide

10: H₂ / Pd/C / ethanol

11: AcOH / H₂O

12: BOP / acetonitrile

With dmap; sodium hydroxide; potassium permanganate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; hydrogen; sodium ethanolate; acetic anhydride; magnesium sulfate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1246/cl.1997.1203

upstream raw materials:

ethyl 2-(pyridin-3-yl) thiazole-4-carboxylate

2-(1-Oxy-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester

2-(6-Cyano-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester

5-(4-Ethoxycarbonyl-thiazol-2-yl)-pyridine-2-carboxylic acid ethyl ester

Downstream raw materials:

6-[2-(1-Benzyloxycarbonylamino-vinyl)-oxazol-4-yl]-5-(4-ethoxycarbonyl-thiazol-2-yl)-pyridine-2-carboxylic acid ethyl ester

6-[2-(1-Benzyloxycarbonylamino-vinyl)-4,5-dihydro-oxazol-4-yl]-5-(4-ethoxycarbonyl-thiazol-2-yl)-pyridine-2-carboxylic acid ethyl ester