(S)-2-tert-Butoxycarbonylamino-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-propionic acid 4-nitro-phenyl ester

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-propionic acid 4-nitro-phenyl ester
• CAS No.: 148101-27-3
• Molecular Formula: C₂₀H₂₄N₄O₉
• Molecular Weight: 464.432
• Mol file: 148101-27-3.mol

Synonyms:

Chemical Property of (S)-2-tert-Butoxycarbonylamino-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-propionic acid 4-nitro-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-tert-Butoxycarbonylamino-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-propionic acid 4-nitro-phenyl ester

There total 4 articles about (S)-2-tert-Butoxycarbonylamino-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-propionic acid 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:

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) → (S)-2-tert-Butoxycarbonylamino-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-propionic acid 4-nitro-phenyl ester (148101-27-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / Bz₂O₂ / acetonitrile / 0 °C

2: 72 percent / NBS, 4 Angstroem molecular sieves / CH₂Cl₂ / Ambient temperature

3: NaOH / methanol / 0 °C

4: DCC, HOBt / ethyl acetate / Ambient temperature

With sodium hydroxide; N-Bromosuccinimide; 4 A molecular sieve; benzotriazol-1-ol; dicyclohexyl-carbodiimide; dibenzoyl peroxide; In methanol; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4039(00)91773-8

Reference yield:

(S)-2-tert-Butoxycarbonylamino-3-methylsulfanylmethoxy-propionic acid methyl ester (148101-19-3) → (S)-2-tert-Butoxycarbonylamino-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-propionic acid 4-nitro-phenyl ester (148101-27-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / NBS, 4 Angstroem molecular sieves / CH₂Cl₂ / Ambient temperature

2: NaOH / methanol / 0 °C

3: DCC, HOBt / ethyl acetate / Ambient temperature

With sodium hydroxide; N-Bromosuccinimide; 4 A molecular sieve; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(00)91773-8

Reference yield:

(S)-2-tert-Butoxycarbonylamino-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-propionic acid methyl ester (148101-25-1) → (S)-2-tert-Butoxycarbonylamino-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-propionic acid 4-nitro-phenyl ester (148101-27-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOH / methanol / 0 °C

2: DCC, HOBt / ethyl acetate / Ambient temperature

With sodium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In methanol; ethyl acetate;

DOI:10.1016/S0040-4039(00)91773-8

upstream raw materials:

4-nitro-phenol

(S)-2-tert-Butoxycarbonylamino-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-propionic acid

N-tert-butyloxycarbonyl-L-serine methyl ester

(S)-2-tert-Butoxycarbonylamino-3-methylsulfanylmethoxy-propionic acid methyl ester

Downstream raw materials:

[(S)-2-tert-Butoxycarbonylamino-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-propionylamino]-acetic acid 4-nitro-phenyl ester