(S)-2-[(S)-2-Acetylamino-3-(2-amino-5-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-[(S)-2-Acetylamino-3-(2-amino-5-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester
• CAS No.: 1028260-79-8
• Molecular Formula: C₁₅H₂₁N₃O₅
• Molecular Weight: 323.349
• Mol file: 1028260-79-8.mol

Synonyms:(S)-2-[(S)-2-Acetylamino-3-(2-amino-5-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester

Chemical Property of (S)-2-[(S)-2-Acetylamino-3-(2-amino-5-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(S)-2-Acetylamino-3-(2-amino-5-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester

There total 16 articles about (S)-2-[(S)-2-Acetylamino-3-(2-amino-5-hydroxy-phenyl)-propionylamino]-propionic 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:

Ac-L-m-Nip(Bn)-Ala-OMe (168702-67-8) → (S)-2-[(S)-2-Acetylamino-3-(2-amino-5-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester (1028260-79-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; acetic acid; under 3.0002 Torr; Ambient temperature;

DOI:10.1021/jo00108a023

Reference yield:

(5-(benzyloxy)-2-nitrophenyl)methanol (68423-36-9) → (S)-2-[(S)-2-Acetylamino-3-(2-amino-5-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester (1028260-79-8)

Guidance literature:

Multi-step reaction with 10 steps

1: Et₃N / tetrahydrofuran / 1 h / 0 °C

2: NaI / acetone / 2 h / Ambient temperature

3: 95 percent / 10percent aq. NaOH, tetrabutylammonium hydrogen sulfate / CH₂Cl₂

4: 98 percent / 1 N aq. HCl, Et₃N / 1.) THF, r.t., 10 min, 2.) MeOH, r.t., 4 h

5: 1 N LiOH / tetrahydrofuran / 0.5 h / Ambient temperature

6: DCC / CH₂Cl₂ / 2 h / -10 °C

7: N-methylmorpholine / dimethylformamide

8: TFA / CH₂Cl₂

9: Et₃N / methanol

10: H₂ / 10percent Pd/C / methanol; acetic acid / 3 Torr / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; sodium hydroxide; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00108a023

Reference yield:

3-hydroxymethyl-4-nitrophenol (60463-12-9) → (S)-2-[(S)-2-Acetylamino-3-(2-amino-5-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester (1028260-79-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 92 percent / NaH / tetrahydrofuran; dimethylformamide / 1.) 30-40 deg C, 30 min, 2.) r.t., 2 h

2: Et₃N / tetrahydrofuran / 1 h / 0 °C

3: NaI / acetone / 2 h / Ambient temperature

4: 95 percent / 10percent aq. NaOH, tetrabutylammonium hydrogen sulfate / CH₂Cl₂

5: 98 percent / 1 N aq. HCl, Et₃N / 1.) THF, r.t., 10 min, 2.) MeOH, r.t., 4 h

6: 1 N LiOH / tetrahydrofuran / 0.5 h / Ambient temperature

7: DCC / CH₂Cl₂ / 2 h / -10 °C

8: N-methylmorpholine / dimethylformamide

9: TFA / CH₂Cl₂

10: Et₃N / methanol

11: H₂ / 10percent Pd/C / methanol; acetic acid / 3 Torr / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; sodium hydroxide; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00108a023

upstream raw materials:

Ac-L-m-Nip(Bn)-Ala-OMe

(5-(benzyloxy)-2-nitrophenyl)methanol

3-hydroxymethyl-4-nitrophenol

5-(Benzyloxy)-2-nitrobenzyl iodide