(S)-ethyl 6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-carboxylate

Base Information

• Chemical Name: (S)-ethyl 6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-carboxylate
• CAS No.: 205648-20-0
• Molecular Formula: C₂₇H₃₃N₃O₆
• Molecular Weight: 495.576
• Mol file: 205648-20-0.mol

Synonyms:(S)-ethyl 6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-carboxylate

Chemical Property of (S)-ethyl 6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-ethyl 6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-carboxylate

There total 9 articles about (S)-ethyl 6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-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:

tert-butyl (1S)-2-amino-1-methyl-2-oxoethylcarbamate (78981-25-6,81587-17-9,85642-13-3) → (S)-ethyl 6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-carboxylate (205648-20-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / dirhodium(II) acetate / CHCl₃ / Heating

2: 70 percent / triethylamine; triphenylphosphine; iodine / CH₂Cl₂ / 20 °C

3: 95 percent / aq. LiOH / methanol / 5 h / 20 °C

4: triethylamine / tetrahydrofuran / 0.33 h / 0 °C

5: tetrahydrofuran / 20 °C

6: 85 percent / ammonium acetate / benzene; acetic acid / 24 h / Heating

7: ethanol / 50 °C

8: 0.5 h / 140 °C

With ammonium acetate; lithium hydroxide; iodine; triethylamine; triphenylphosphine; dirhodium tetraacetate; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; acetic acid; benzene; 1: Condensation / 2: Cyclization / 3: Hydrolysis / 4: Carboxylation / 5: Substitution / 6: Amination / 7: Condensation / 8: Cyclization;

DOI:10.1021/ja994247b

Reference yield:

(S)-2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazole-4-carboxylic acid (205648-17-5) → (S)-ethyl 6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-carboxylate (205648-20-0)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / tetrahydrofuran / 0.33 h / 0 °C

2: tetrahydrofuran / 20 °C

3: 85 percent / ammonium acetate / benzene; acetic acid / 24 h / Heating

4: ethanol / 50 °C

5: 0.5 h / 140 °C

With ammonium acetate; triethylamine; In tetrahydrofuran; ethanol; acetic acid; benzene; 1: Carboxylation / 2: Substitution / 3: Amination / 4: Condensation / 5: Cyclization;

DOI:10.1021/ja994247b

Reference yield:

(S)-ethyl 3-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}-3-oxopropanoate (205648-18-6) → (S)-ethyl 6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-carboxylate (205648-20-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / ammonium acetate / benzene; acetic acid / 24 h / Heating

2: ethanol / 50 °C

3: 0.5 h / 140 °C

With ammonium acetate; In ethanol; acetic acid; benzene; 1: Amination / 2: Condensation / 3: Cyclization;

DOI:10.1021/ja994247b

upstream raw materials:

1-(benzyloxy)but-3-yn-2-one

(S)-ethyl 3-amino-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}propenoate

tert-butyl (1S)-2-amino-1-methyl-2-oxoethylcarbamate

N-(tert-butoxycarbonyl)-N'-[2-(1-methoxycarbonyl-3-oxobutyl)]-S-alaninamide

Downstream raw materials:

2-({(S)-2-[(2-{6-Benzyloxymethyl-2-[2-((S)-1-tert-butoxycarbonylamino-ethyl)-5-methyl-oxazol-4-yl]-pyridin-3-yl}-thiazole-4-carbonyl)-amino]-3-methyl-butyrylamino}-methyl)-5-methyl-oxazole-4-carboxylic acid methyl ester

C₄₀H₄₁N₉O₇S₂

2-{6-Benzyloxymethyl-2-[2-((S)-1-tert-butoxycarbonylamino-ethyl)-5-methyl-oxazol-4-yl]-pyridin-3-yl}-thiazole-4-carboxylic acid

(S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}-3-(4-ethoxycarbonylthiazol-2-yl)pyridine