(S)-N-(6-hydroxy-1-oxo-2-phthalimidohexyl)-D-phenylalanine ethyl ester

Base Information

• Chemical Name: (S)-N-(6-hydroxy-1-oxo-2-phthalimidohexyl)-D-phenylalanine ethyl ester
• CAS No.: 155012-89-8
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.507
• Mol file: 155012-89-8.mol

Synonyms:(S)-N-(6-hydroxy-1-oxo-2-phthalimidohexyl)-D-phenylalanine ethyl ester

Chemical Property of (S)-N-(6-hydroxy-1-oxo-2-phthalimidohexyl)-D-phenylalanine ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-(6-hydroxy-1-oxo-2-phthalimidohexyl)-D-phenylalanine ethyl ester

There total 3 articles about (S)-N-(6-hydroxy-1-oxo-2-phthalimidohexyl)-D-phenylalanine ethyl 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: 99.0%

D-phenylalanine ethyl ester hydrochloride (63060-94-6) + (S)-2-(1,3-dioxoisoindolin-2-yl)-6-hydroxyhexanoic acid (84688-11-9) → (S)-N-(6-hydroxy-1-oxo-2-phthalimidohexyl)-D-phenylalanine ethyl ester (155012-89-8)

Guidance literature:

With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2.5h;

DOI:10.1021/ja00085a014

Reference yield:

(S)-2-amino-6-hydroxyhexanoic acid (6033-32-5) → (S)-N-(6-hydroxy-1-oxo-2-phthalimidohexyl)-D-phenylalanine ethyl ester (155012-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / Na₂CO₃ / H₂O / 2 h / Ambient temperature

2: 99 percent / 4-methylmorpholine, 1-hydroxybenzotriazole hydrate, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride / dimethylformamide / 2.5 h / 0 - 20 °C

With 4-methyl-morpholine; sodium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In water; N,N-dimethyl-formamide;

DOI:10.1021/ja00085a014

Reference yield:

N-ethoxycarbonylphthalimide (22509-74-6) → (S)-N-(6-hydroxy-1-oxo-2-phthalimidohexyl)-D-phenylalanine ethyl ester (155012-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / Na₂CO₃ / H₂O / 2 h / Ambient temperature

2: 99 percent / 4-methylmorpholine, 1-hydroxybenzotriazole hydrate, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride / dimethylformamide / 2.5 h / 0 - 20 °C

With 4-methyl-morpholine; sodium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In water; N,N-dimethyl-formamide;

DOI:10.1021/ja00085a014

upstream raw materials:

D-phenylalanine ethyl ester hydrochloride

(S)-2-(1,3-dioxoisoindolin-2-yl)-6-hydroxyhexanoic acid

(S)-2-amino-6-hydroxyhexanoic acid

N-ethoxycarbonylphthalimide

Downstream raw materials:

(S)-N-(1,6-dioxo-2-phthalimidohexyl)-D-phenylalanine ethyl ester