[3-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-tert-butoxycarbonylamino-piperidin-1-yl]-acetic acid ethyl ester

Base Information

• Chemical Name: [3-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-tert-butoxycarbonylamino-piperidin-1-yl]-acetic acid ethyl ester
• CAS No.: 708253-93-4
• Molecular Formula: C₂₆H₃₄N₄O₇
• Molecular Weight: 514.579
• Mol file: 708253-93-4.mol

Synonyms:

Chemical Property of [3-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-tert-butoxycarbonylamino-piperidin-1-yl]-acetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-tert-butoxycarbonylamino-piperidin-1-yl]-acetic acid ethyl ester

There total 10 articles about [3-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-tert-butoxycarbonylamino-piperidin-1-yl]-acetic 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:

(3R,5R)-1-benzyl-5-[(tert-butyldimethylsilyl)oxy]-piperidin-3-ol (161564-09-6) → [3-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-tert-butoxycarbonylamino-piperidin-1-yl]-acetic acid ethyl ester (708253-93-4)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine

2: NaN₃ / dimethylformamide / 65 °C

3: H₂ / Ra-Ni

4: H₂ / Pd/C

5: diisopropylethylamine

6: TBAF / tetrahydrofuran

7: PPh₃; DIAD

With pyridine; sodium azide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; Ra-Ni; In tetrahydrofuran; N,N-dimethyl-formamide; 8: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2004.02.034

Reference yield:

(2S,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]-oxy}-1-benzyl-2-hydroxy-methyl-pyrrolidin (154343-02-9) → [3-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-tert-butoxycarbonylamino-piperidin-1-yl]-acetic acid ethyl ester (708253-93-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: trifluoroacetic anhydride

1.2: diisopropylethylamine

2.1: pyridine

3.1: NaN₃ / dimethylformamide / 65 °C

4.1: H₂ / Ra-Ni

5.1: H₂ / Pd/C

6.1: diisopropylethylamine

7.1: TBAF / tetrahydrofuran

8.1: PPh₃; DIAD

With pyridine; sodium azide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic anhydride; palladium on activated charcoal; Ra-Ni; In tetrahydrofuran; N,N-dimethyl-formamide; 9.1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2004.02.034

Reference yield:

(2S,4R)-1-benzyl-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid methyl ester (154429-40-0) → [3-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-tert-butoxycarbonylamino-piperidin-1-yl]-acetic acid ethyl ester (708253-93-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: LiBH₄ / tetrahydrofuran

2.1: trifluoroacetic anhydride

2.2: diisopropylethylamine

3.1: pyridine

4.1: NaN₃ / dimethylformamide / 65 °C

5.1: H₂ / Ra-Ni

6.1: H₂ / Pd/C

7.1: diisopropylethylamine

8.1: TBAF / tetrahydrofuran

9.1: PPh₃; DIAD

With pyridine; lithium borohydride; sodium azide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic anhydride; palladium on activated charcoal; Ra-Ni; In tetrahydrofuran; N,N-dimethyl-formamide; 10.1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2004.02.034

upstream raw materials:

N-3-benzoylthymine

((3S,5R)-3-tert-Butoxycarbonylamino-5-hydroxy-piperidin-1-yl)-acetic acid ethyl ester

(3R,5R)-1-benzyl-5-[(tert-butyldimethylsilyl)oxy]-piperidin-3-ol

(2S,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]-oxy}-1-benzyl-2-hydroxy-methyl-pyrrolidin