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

Base Information

Chemical Name:(2S,4S)-4-Acetylthio-2-(methylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
CAS No.:127767-95-7
Molecular Formula:C₁₈H₂₃N₃O₇S
Molecular Weight:425.463
Hs Code.:

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

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

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

There total 13 articles about (2S,4S)-4-Acetylthio-2-(methylcarbamoyl)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: 71.0%

: 507-09-5
tiolacetic acid

: 127767-89-9
(2S,4R)-4-methanesulfonyloxy-2-(methylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

: 127767-95-7
(2S,4S)-4-Acetylthio-2-(methylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

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:

: 101803-29-6
(2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

: 127767-95-7
(2S,4S)-4-Acetylthio-2-(methylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

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: 71 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:

: 104795-10-0
(2S,4R)-4-tert-butyldimethylsiloxy-2-hydroxymethyl-N-(4-nitrobenzyloxycarbonyl) pyrrolidine

: 127767-95-7
(2S,4S)-4-Acetylthio-2-(methylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

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: 71 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