(S)-2-((R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid ethyl ester

Base Information

• Chemical Name: (S)-2-((R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid ethyl ester
• CAS No.: 113955-29-6
• Molecular Formula: C₂₇H₃₄N₂O₅S₂
• Molecular Weight: 530.709
• Mol file: 113955-29-6.mol

Synonyms:(S)-2-((R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid ethyl ester

Chemical Property of (S)-2-((R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid ethyl ester

There total 11 articles about (S)-2-((R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid 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: 98.0%

(R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester (109010-59-5) + ((R)-6-Amino-5-oxo-2-thiophen-2-yl-6,7-dihydro-5H-[1,4]thiazepin-4-yl)-acetic acid tert-butyl ester (113955-35-4) → (S)-2-((R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid ethyl ester (113955-29-6)

Guidance literature:

With triethylamine; In various solvent(s); at 50 ℃; for 24h;

DOI:10.1246/cl.1989.137

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-2-((R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid ethyl ester (113955-29-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / Et₃N / dimethylformamide / 3 h / Ambient temperature

2: 98 percent / NaH / dimethylformamide / 1.) 5 deg C to RT, 1 h; 2.) 1 h

3: 72 percent / N-methylmorpholine, tert-butyl hypochlorite / toluene / 1.) from -40- -50 deg C to RT, 3 h; 2.) 2 h

4: 99 percent / p-TSA*H₂O / dioxane / 6 h / Ambient temperature

5: 98 percent / Et₃N / various solvent(s) / 24 h / 50 °C

With 4-methyl-morpholine; tert-butylhypochlorite; sodium hydride; toluene-4-sulfonic acid; triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide; toluene;

DOI:10.1246/cl.1989.137

Reference yield:

((2R,6R)-5-Oxo-2-thiophen-2-yl-[1,4]thiazepan-6-yl)-carbamic acid tert-butyl ester (110221-23-3) → (S)-2-((R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid ethyl ester (113955-29-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / NaH / dimethylformamide / 1.) 5 deg C to RT, 1 h; 2.) 1 h

2: 72 percent / N-methylmorpholine, tert-butyl hypochlorite / toluene / 1.) from -40- -50 deg C to RT, 3 h; 2.) 2 h

3: 99 percent / p-TSA*H₂O / dioxane / 6 h / Ambient temperature

4: 98 percent / Et₃N / various solvent(s) / 24 h / 50 °C

With 4-methyl-morpholine; tert-butylhypochlorite; sodium hydride; toluene-4-sulfonic acid; triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide; toluene;

DOI:10.1246/cl.1989.137

upstream raw materials:

(R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester

((R)-6-Amino-5-oxo-2-thiophen-2-yl-6,7-dihydro-5H-[1,4]thiazepin-4-yl)-acetic acid tert-butyl ester

bromoacetic acid tert-butyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

(S)-2-((R)-4-Carboxymethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid ethyl ester

(S)-2-((R)-4-Carboxymethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid