N^α-(benzyloxycarbonyl)-N^im-(2,4-dinitrophenyl)-erythro-β-hydroxy-L-histidine

Base Information

• Chemical Name: N^α-(benzyloxycarbonyl)-N^im-(2,4-dinitrophenyl)-erythro-β-hydroxy-L-histidine
• CAS No.: 140480-22-4
• Molecular Formula: C₂₀H₁₇N₅O₉
• Molecular Weight: 471.383
• Mol file: 140480-22-4.mol

Synonyms:N^α-(benzyloxycarbonyl)-N^im-(2,4-dinitrophenyl)-erythro-β-hydroxy-L-histidine

Chemical Property of N^α-(benzyloxycarbonyl)-N^im-(2,4-dinitrophenyl)-erythro-β-hydroxy-L-histidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^α-(benzyloxycarbonyl)-N^im-(2,4-dinitrophenyl)-erythro-β-hydroxy-L-histidine

There total 1 articles about N^α-(benzyloxycarbonyl)-N^im-(2,4-dinitrophenyl)-erythro-β-hydroxy-L-histidine 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: 76.0%

2,4-Dinitrofluorobenzene (70-34-8,65727-75-5) + Nα-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidine (101485-34-1) → Nα-(benzyloxycarbonyl)-Nim-(2,4-dinitrophenyl)-erythro-β-hydroxy-L-histidine (140480-22-4)

Guidance literature:

With sodium hydrogencarbonate; In methanol; water; for 16h; Ambient temperature;

DOI:10.1016/S0040-4020(01)90783-5

Reference yield:

Nα-(benzyloxycarbonyl)-Nim-(2,4-dinitrophenyl)-erythro-β-hydroxy-L-histidine (140480-22-4) → (S)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridyl>carbonyl>-erythro-β-tert-butoxy-L-histidyl>amino>pentanoic acid (123993-14-6,140632-66-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 4-methylmorpholine, EDCI, HOBT*H₂O / dimethylformamide / 14 h / Ambient temperature

2: 3-mercaptopropionic acid / tetrahydrofuran / 1 h / Ambient temperature

3: 80 percent / conc. H₂SO₄ / CH₂Cl₂ / 72 h / Ambient temperature

4: 100 percent / 1) HCOOH, 2) HCl / 1) Pd black / ethanol / 1) 1h, RT, 2) toluene

5: NEt₃, DPPA / dimethylformamide / 12 h / Ambient temperature

6: 69 percent / 0.5N NaOH / methanol / 28 h / 0 - 4 °C

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; formic acid; sulfuric acid; diphenyl-phosphinic acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-mercaptopropionic acid; palladium; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)90783-5

Reference yield:

Nα-(benzyloxycarbonyl)-Nim-(2,4-dinitrophenyl)-erythro-β-hydroxy-L-histidine (140480-22-4) → ethyl (S)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridyl>carbonyl>-erythro-β-tert-butoxy-L-histidyl>amino>pentanoate (140480-27-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 4-methylmorpholine, EDCI, HOBT*H₂O / dimethylformamide / 14 h / Ambient temperature

2: 3-mercaptopropionic acid / tetrahydrofuran / 1 h / Ambient temperature

3: 80 percent / conc. H₂SO₄ / CH₂Cl₂ / 72 h / Ambient temperature

4: 100 percent / 1) HCOOH, 2) HCl / 1) Pd black / ethanol / 1) 1h, RT, 2) toluene

5: NEt₃, DPPA / dimethylformamide / 12 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; formic acid; sulfuric acid; diphenyl-phosphinic acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-mercaptopropionic acid; palladium; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)90783-5

upstream raw materials:

2,4-Dinitrofluorobenzene

N^α-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidine

Downstream raw materials:

ethyl (S)-4-<α-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidyl>amino>pentanoate

ethyl (S)-4-<α-(benzyloxycarbonyl)-erythro-β-tert-butoxy-L-histidyl>amino>pentanoate

(S)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridyl>carbonyl>-erythro-β-tert-butoxy-L-histidyl>amino>pentanoic acid

ethyl (S)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridyl>carbonyl>-erythro-β-tert-butoxy-L-histidyl>amino>pentanoate