3-(4-[N_α-tert-butoxycarbonyl-L-leucinoylamino]phenyl)propanoic acid methyl ester

Base Information

• Chemical Name: 3-(4-[N_α-tert-butoxycarbonyl-L-leucinoylamino]phenyl)propanoic acid methyl ester
• CAS No.: 391610-79-0
• Molecular Formula: C₂₁H₃₂N₂O₅
• Molecular Weight: 392.495

Synonyms:3-(4-[N_α-tert-butoxycarbonyl-L-leucinoylamino]phenyl)propanoic acid methyl ester

Chemical Property of 3-(4-[N_α-tert-butoxycarbonyl-L-leucinoylamino]phenyl)propanoic acid methyl ester

Chemical Property:

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Technology Process of 3-(4-[N_α-tert-butoxycarbonyl-L-leucinoylamino]phenyl)propanoic acid methyl ester

There total 2 articles about 3-(4-[N_α-tert-butoxycarbonyl-L-leucinoylamino]phenyl)propanoic acid methyl 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: 50.0%

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) + methyl 3-(4-aminophenyl)propionate (35418-07-6) → 3-(4-[Nα-tert-butoxycarbonyl-L-leucinoylamino]phenyl)propanoic acid methyl ester (391610-79-0)

Guidance literature:

N-tert-butoxycarbonyl-L-leucine; With 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine; In tetrahydrofuran; at -78 ℃; for 0.5h;

methyl 3-(4-aminophenyl)propionate; With pyridine; In tetrahydrofuran; at -78 - 20 ℃; for 1h; Further stages.;

DOI:10.1021/jm010985a

Reference yield:

trans-p-aminocinnamic acid (17570-30-8) → 3-(4-[Nα-tert-butoxycarbonyl-L-leucinoylamino]phenyl)propanoic acid methyl ester (391610-79-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: H₂ / 10percent Pd/C / 2-methoxy-ethanol / 3 h / 20 °C / 3040.2 Torr

2.1: SOCl₂ / 20 °C

3.1: PPh₃; hexachloroacetone / tetrahydrofuran / 0.5 h / -78 °C

3.2: 50 percent / pyridine / tetrahydrofuran / 1 h / -78 - 20 °C

With thionyl chloride; 1,1,1,3,3,3-hexachloro-propan-2-one; hydrogen; triphenylphosphine; 10percent Pd/C; In tetrahydrofuran; 2-methoxy-ethanol;

DOI:10.1021/jm010985a

Reference yield: 99.0%

3-(4-[Nα-tert-butoxycarbonyl-L-leucinoylamino]phenyl)propanoic acid methyl ester (391610-79-0) → 3-(4-[Nα-tert-butoxycarbonyl-L-leucinoylamino]phenyl)propanoic acid (216371-80-1)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 0.166667h;

DOI:10.1021/jm010985a

upstream raw materials:

N-tert-butoxycarbonyl-L-leucine

methyl 3-(4-aminophenyl)propionate

trans-p-aminocinnamic acid

Downstream raw materials:

3-(4-[N_α-tert-butoxycarbonyl-L-leucinoylamino]phenyl)propanoic acid

8-O-(3-[4-{N_α-tert-butoxycarbonyl-L-leucinoylamino}phenyl]propanoyl)-8-O-debutanoylthapsigargin

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