carbonic acid 1-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidin-2-ylmethyl ester 4-nitro-phenyl ester

Base Information

• Chemical Name: carbonic acid 1-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidin-2-ylmethyl ester 4-nitro-phenyl ester
• CAS No.: 380648-98-6
• Molecular Formula: C₃₁H₃₄N₆O₁₁
• Molecular Weight: 666.645
• Mol file: 380648-98-6.mol

Synonyms:

Chemical Property of carbonic acid 1-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidin-2-ylmethyl ester 4-nitro-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of carbonic acid 1-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidin-2-ylmethyl ester 4-nitro-phenyl ester

There total 10 articles about carbonic acid 1-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidin-2-ylmethyl ester 4-nitro-phenyl 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:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) → carbonic acid 1-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidin-2-ylmethyl ester 4-nitro-phenyl ester (380648-98-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / pyridine / cooling

2: 98.5 percent / NaN₃ / dimethylformamide / 8 h / 70 °C

3: H₂ / Raney Nickel / methanol; H₂O / 1.5 h / 2068.59 Torr

4: 3.17 g / Et₃N / dimethylsulfoxide / 8 h

5: 70 percent / LiBH₄ / tetrahydrofuran / 3.5 h

6: H₂ / Pd-C / methanol / 7 h / 3102.89 Torr

7: 1.85 g / HOBt; DCC / dimethylformamide / 6 h / 20 °C

8: 53 percent / Et₃N / dioxane

With pyridine; lithium borohydride; sodium azide; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00331-6

Reference yield:

4(S)-azido-N-<(phenylmethoxy)carbonyl>-(S)-proline methyl ester (113490-74-7) → carbonic acid 1-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidin-2-ylmethyl ester 4-nitro-phenyl ester (380648-98-6)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / Raney Nickel / methanol; H₂O / 1.5 h / 2068.59 Torr

2: 3.17 g / Et₃N / dimethylsulfoxide / 8 h

3: 70 percent / LiBH₄ / tetrahydrofuran / 3.5 h

4: H₂ / Pd-C / methanol / 7 h / 3102.89 Torr

5: 1.85 g / HOBt; DCC / dimethylformamide / 6 h / 20 °C

6: 53 percent / Et₃N / dioxane

With lithium borohydride; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00331-6

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate (117811-78-6) → carbonic acid 1-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidin-2-ylmethyl ester 4-nitro-phenyl ester (380648-98-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 98.5 percent / NaN₃ / dimethylformamide / 8 h / 70 °C

2: H₂ / Raney Nickel / methanol; H₂O / 1.5 h / 2068.59 Torr

3: 3.17 g / Et₃N / dimethylsulfoxide / 8 h

4: 70 percent / LiBH₄ / tetrahydrofuran / 3.5 h

5: H₂ / Pd-C / methanol / 7 h / 3102.89 Torr

6: 1.85 g / HOBt; DCC / dimethylformamide / 6 h / 20 °C

7: 53 percent / Et₃N / dioxane

With lithium borohydride; sodium azide; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00331-6

upstream raw materials:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

4(S)-azido-N-<(phenylmethoxy)carbonyl>-(S)-proline methyl ester

methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate

tert-butyl ((3S,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate