11-thiohomoaminopterin

Base Information

• Chemical Name: 11-thiohomoaminopterin
• CAS No.: 74163-10-3
• Molecular Formula: C20H21 N7 O5 S
• Molecular Weight: 471.49
• Mol file: 74163-10-3.mol

Synonyms:11-thiohomoaminopterin

Chemical Property of 11-thiohomoaminopterin

Chemical Property:

• PSA: 232.60000
• Density: 1.57g/cm³
• LogP: 2.52010

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 11-thiohomoaminopterin

There total 19 articles about 11-thiohomoaminopterin 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:

1-chloro-4--2-butanone (67426-03-3) → 11-thiohomoaminopterin (74163-10-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 91 percent / sodium azide, potassium iodide / acetone

2: 85 percent / p-toluenesulfonic acid / benzene / 6 h / Heating

3: H₂ / 5percent Pd/C / methanol / 18 h / 1189.4 Torr

4: 78 percent / N-methylmorpholine / methanol / 4 h / Heating

5: 94 percent / trifluoroacetic acid (TFA) / 50 °C

6: 80 percent / sodium dithionite / dioxane

7: 750 mg / pyridine, concd. HCl / methanol / 1 h / Heating

8: dimethylformamide / 2 h / 120 °C

9: 240 mg / NaOH / acetonitrile / 4 h

10: N-methylmorpholine / dimethylsulfoxide; tetrahydrofuran / 0.33 h / 0 - 25 °C

11: N-methylmorpholine / dimethylsulfoxide; tetrahydrofuran / 18 h / 25 °C

12: NaOH / acetonitrile / 4 h

With 4-methyl-morpholine; pyridine; hydrogenchloride; sodium hydroxide; sodium azide; sodium dithionite; hydrogen; toluene-4-sulfonic acid; N,N-dimethyl-formamide; trifluoroacetic acid; potassium iodide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dimethyl sulfoxide; acetone; acetonitrile; benzene;

DOI:10.1021/jm00182a017

Reference yield:

1-azido-4--2-butanone (74162-96-2) → 11-thiohomoaminopterin (74163-10-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / p-toluenesulfonic acid / benzene / 6 h / Heating

2: H₂ / 5percent Pd/C / methanol / 18 h / 1189.4 Torr

3: 78 percent / N-methylmorpholine / methanol / 4 h / Heating

4: 94 percent / trifluoroacetic acid (TFA) / 50 °C

5: 80 percent / sodium dithionite / dioxane

6: 750 mg / pyridine, concd. HCl / methanol / 1 h / Heating

7: dimethylformamide / 2 h / 120 °C

8: 240 mg / NaOH / acetonitrile / 4 h

9: N-methylmorpholine / dimethylsulfoxide; tetrahydrofuran / 0.33 h / 0 - 25 °C

10: N-methylmorpholine / dimethylsulfoxide; tetrahydrofuran / 18 h / 25 °C

11: NaOH / acetonitrile / 4 h

With 4-methyl-morpholine; pyridine; hydrogenchloride; sodium hydroxide; sodium dithionite; hydrogen; toluene-4-sulfonic acid; N,N-dimethyl-formamide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dimethyl sulfoxide; acetonitrile; benzene;

DOI:10.1021/jm00182a017

Reference yield:

4-[2-(2-Azidomethyl-[1,3]dioxolan-2-yl)-ethylsulfanyl]-benzoic acid (74162-98-4) → 11-thiohomoaminopterin (74163-10-3)

Guidance literature:

Multi-step reaction with 9 steps

1: N-methylmorpholine / 0.33 h

2: N-methylmorpholine / dimethylformamide / 18 h

3: H₂ / 5percent Pd/C

4: N-methylmorpholine / methanol / 4 h / Heating

5: trifluoroacetic acid (TFA) / 0.5 h / 50 °C

6: sodium dithionite / dioxane

7: pyridine, concd. HCl / methanol / 1 h / Heating

8: dimethylformamide / 2 h / 120 °C

9: NaOH / acetonitrile / 4 h

With 4-methyl-morpholine; pyridine; hydrogenchloride; sodium hydroxide; sodium dithionite; hydrogen; N,N-dimethyl-formamide; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm00182a017

upstream raw materials:

1-chloro-4--2-butanone

4-[2-(2-Aminomethyl-[1,3]dioxolan-2-yl)-ethylsulfanyl]-benzoic acid methyl ester

1-azido-4--2-butanone

4-[2-(2-Azidomethyl-[1,3]dioxolan-2-yl)-ethylsulfanyl]-benzoic acid

Refernces