(2S,4S)-4-Acetylthio-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Base Information

• Chemical Name: (2S,4S)-4-Acetylthio-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
• CAS No.: 127767-94-6
• Molecular Formula: C₁₉H₂₅N₃O₇S
• Molecular Weight: 439.489

Synonyms:(2S,4S)-4-Acetylthio-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Chemical Property of (2S,4S)-4-Acetylthio-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-4-Acetylthio-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

There total 13 articles about (2S,4S)-4-Acetylthio-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 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: 72.0%

tiolacetic acid (507-09-5) + (2S,4R)-2-(dimethylcarbamoyl)methyloxymethyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (127767-88-8) → (2S,4S)-4-Acetylthio-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (127767-94-6)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 75 - 80 ℃; for 3h;

DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

(2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (101803-29-6) → (2S,4S)-4-Acetylthio-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (127767-94-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

2: 48 percent / NaBH₄ / ethanol / 16 h / Ambient temperature

3: H₂ / 20percent Pd(OH)2/C / methanol / 3 h / 760 Torr / Ambient temperature

4: aq. NaOH / tetrahydrofuran / 2 h

5: 94 percent / NaH / tetrahydrofuran / 3 h / Ambient temperature

6: aq. 6N HCl / 3 h / Heating

7: 4N aq. NaOH / tetrahydrofuran; H₂O / 2 h

8: 75 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

9: POCl₃ / dimethylformamide; tetrahydrofuran / 0.5 h / 0 - 10 °C

10: Et₃N / dimethylformamide; tetrahydrofuran; methanol / 2 h / Ambient temperature

11: 72 percent / t-BuOK / dimethylformamide / 3 h / 75 - 80 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; potassium tert-butylate; hydrogen; sodium hydride; triethylamine; trichlorophosphate; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

(2S,4R)-4-tert-butyldimethylsiloxy-2-hydroxymethyl-N-(4-nitrobenzyloxycarbonyl) pyrrolidine (104795-10-0) → (2S,4S)-4-Acetylthio-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (127767-94-6)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂ / 20percent Pd(OH)2/C / methanol / 3 h / 760 Torr / Ambient temperature

2: aq. NaOH / tetrahydrofuran / 2 h

3: 94 percent / NaH / tetrahydrofuran / 3 h / Ambient temperature

4: aq. 6N HCl / 3 h / Heating

5: 4N aq. NaOH / tetrahydrofuran; H₂O / 2 h

6: 75 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

7: POCl₃ / dimethylformamide; tetrahydrofuran / 0.5 h / 0 - 10 °C

8: Et₃N / dimethylformamide; tetrahydrofuran; methanol / 2 h / Ambient temperature

9: 72 percent / t-BuOK / dimethylformamide / 3 h / 75 - 80 °C

With hydrogenchloride; sodium hydroxide; potassium tert-butylate; hydrogen; sodium hydride; triethylamine; trichlorophosphate; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(97)00142-9

upstream raw materials:

tiolacetic acid

(2S,4R)-2-(dimethylcarbamoyl)methyloxymethyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

(2S,4R)-4-t-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine

(2S,4R)-2-carboxymethyloxymethyl-4-hydroxypyrrolidine

Downstream raw materials:

4-Nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

(2S,4S)-2-(Dimethylcarbamoyl)methyloxymethyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 127767-94-6 (2S,4S)-4-Acetylthio-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Send

Send

Metric Ton KG G Pound L ML

Send

Send