(3R,4R)-4-[3-(5-acetyl-4-methyl-thiazol-2-yl)-ureido]-3-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid t-butyl ester

Base Information

• Chemical Name: (3R,4R)-4-[3-(5-acetyl-4-methyl-thiazol-2-yl)-ureido]-3-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid t-butyl ester
• CAS No.: 388097-48-1
• Molecular Formula: C₃₀H₄₂FN₅O₄S
• Molecular Weight: 587.759
• Mol file: 388097-48-1.mol

Synonyms:

Chemical Property of (3R,4R)-4-[3-(5-acetyl-4-methyl-thiazol-2-yl)-ureido]-3-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid t-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-4-[3-(5-acetyl-4-methyl-thiazol-2-yl)-ureido]-3-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid t-butyl ester

There total 8 articles about (3R,4R)-4-[3-(5-acetyl-4-methyl-thiazol-2-yl)-ureido]-3-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid t-butyl 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:

C31H42FN3O3 → (3R,4R)-4-[3-(5-acetyl-4-methyl-thiazol-2-yl)-ureido]-3-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid t-butyl ester (388097-48-1)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd(OH)2/C / ethanol / 20 °C / 3102.97 Torr

2: BH₃ / tetrahydrofuran / 20 °C

3: acetonitrile

With borane; hydrogen; palladium dihydroxide; In tetrahydrofuran; ethanol; acetonitrile;

DOI:10.1016/j.bmcl.2007.03.065

Reference yield:

1-tert-butyl 3-ethyl 4-oxopiperidine-1,3-dicarboxylate (98977-34-5) → (3R,4R)-4-[3-(5-acetyl-4-methyl-thiazol-2-yl)-ureido]-3-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid t-butyl ester (388097-48-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: p-TsOH / benzene / Heating

2.1: NaBH(OAc)3; HOAc / acetonitrile / 0 °C

2.2: K₂CO₃ / ethanol / Heating

3.1: tetrahydrofuran / 20 °C / Saponification

4.1: BOP; Et₃N / CH₂Cl₂ / 20 °C

5.1: H₂ / Pd(OH)2/C / ethanol / 20 °C / 3102.97 Torr

6.1: BH₃ / tetrahydrofuran / 20 °C

7.1: acetonitrile

With borane; hydrogen; sodium tris(acetoxy)borohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; acetic acid; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile; benzene;

DOI:10.1016/j.bmcl.2007.03.065

Reference yield:

(S)-3-(4-fluorobenzyl)-piperidine (275815-80-0) → (3R,4R)-4-[3-(5-acetyl-4-methyl-thiazol-2-yl)-ureido]-3-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid t-butyl ester (388097-48-1)

Guidance literature:

Multi-step reaction with 4 steps

1: BOP; Et₃N / CH₂Cl₂ / 20 °C

2: H₂ / Pd(OH)2/C / ethanol / 20 °C / 3102.97 Torr

3: BH₃ / tetrahydrofuran / 20 °C

4: acetonitrile

With borane; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1016/j.bmcl.2007.03.065

upstream raw materials:

(5-acetyl-4-methyl-thiazol-2-yl)-carbamic acid phenyl ester

(3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid t-butyl ester

(3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester

1-tert-butyl 3-ethyl 4-oxopiperidine-1,3-dicarboxylate