(S)-2-((3S,6R)-4-Carboxymethyl-5-oxo-3-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid

Base Information

• Chemical Name: (S)-2-((3S,6R)-4-Carboxymethyl-5-oxo-3-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid
• CAS No.: 102090-06-2
• Molecular Formula: C₂₁H₂₄N₂O₅S₂
• Molecular Weight: 448.564
• Mol file: 102090-06-2.mol

Synonyms:(S)-2-((3S,6R)-4-Carboxymethyl-5-oxo-3-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid

Chemical Property of (S)-2-((3S,6R)-4-Carboxymethyl-5-oxo-3-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((3S,6R)-4-Carboxymethyl-5-oxo-3-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid

There total 12 articles about (S)-2-((3S,6R)-4-Carboxymethyl-5-oxo-3-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid 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: 97.0%

(S)-2-((3S,6R)-4-Carboxymethyl-5-oxo-3-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester; hydrochloride (110221-50-6) → (S)-2-((3S,6R)-4-Carboxymethyl-5-oxo-3-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid (102090-06-2)

Guidance literature:

With sodium hydroxide; for 16h; Ambient temperature;

DOI:10.1021/jm00394a009

Reference yield:

ethyl (R)-2-hydroxy-4-phenylbutyrate (90315-82-5) → (S)-2-((3S,6R)-4-Carboxymethyl-5-oxo-3-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid (102090-06-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: 82 percent / Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

3: 98 percent / 4 N aq. HCl / dioxane / 16 h / Ambient temperature

4: 97 percent / 1 N aq. NaOH / 16 h / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; triethylamine; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jm00394a009

Reference yield:

(E)-2-oxo-4-phenyl-3-butenoic acid (1914-59-6) → (S)-2-((3S,6R)-4-Carboxymethyl-5-oxo-3-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid (102090-06-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / p-toluenesulfonic acid*H₂O / benzene / 5 h / Heating

2: 29 percent / H₂ / 5percent Pd/C / propan-2-ol / 5 h / 50 °C / 2280 Torr

3: 86 percent / KOH / ethanol / 16 h / Ambient temperature

4: 98 percent / conc. H₂SO₄ / 16 h / Ambient temperature

5: 100 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

6: 82 percent / Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

7: 98 percent / 4 N aq. HCl / dioxane / 16 h / Ambient temperature

8: 97 percent / 1 N aq. NaOH / 16 h / Ambient temperature

With pyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; sulfuric acid; hydrogen; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; isopropyl alcohol; benzene;

DOI:10.1021/jm00394a009

upstream raw materials:

(S)-2-((3S,6R)-4-Carboxymethyl-5-oxo-3-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester; hydrochloride

(E)-2-oxo-4-phenyl-3-butenoic acid

R-2-hydroxy-4-phenylbutyric acid L-menthyl ester

(R)-2-hydroxy4-phenylbutanoic acid