(4R,5S,6S)-3-[(3S,5S)-5-Carbamoylmethoxymethyl-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (4R,5S,6S)-3-[(3S,5S)-5-Carbamoylmethoxymethyl-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 199998-96-4
• Molecular Formula: C₃₂H₃₅N₅O₁₂S
• Molecular Weight: 713.722

Synonyms:

Chemical Property of (4R,5S,6S)-3-[(3S,5S)-5-Carbamoylmethoxymethyl-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,6S)-3-[(3S,5S)-5-Carbamoylmethoxymethyl-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 14 articles about (4R,5S,6S)-3-[(3S,5S)-5-Carbamoylmethoxymethyl-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl 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:

(2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (101803-29-6) → (4R,5S,6S)-3-[(3S,5S)-5-Carbamoylmethoxymethyl-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (199998-96-4)

Guidance literature:

Multi-step reaction with 13 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: Et₃N / tetrahydrofuran / 0.5 h / -10 - -5 °C

10: NH₃ / tetrahydrofuran / 0.5 h / 0 °C

11: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, 90 deg C, 3 h

12: NaOMe / methanol / 1 h / -10 - -5 °C

13: i-Pr₂EtN / acetonitrile / a) from -10 deg C to -5 deg C, 1 h, b) from 20 deg C to 25 deg C, 4 h

With 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; ammonia; hydrogen; sodium methylate; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

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

Reference yield:

(2S,4R)-4-tert-butyldimethylsiloxy-2-hydroxymethyl-N-(4-nitrobenzyloxycarbonyl) pyrrolidine (104795-10-0) → (4R,5S,6S)-3-[(3S,5S)-5-Carbamoylmethoxymethyl-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (199998-96-4)

Guidance literature:

Multi-step reaction with 11 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: Et₃N / tetrahydrofuran / 0.5 h / -10 - -5 °C

8: NH₃ / tetrahydrofuran / 0.5 h / 0 °C

9: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, 90 deg C, 3 h

10: NaOMe / methanol / 1 h / -10 - -5 °C

11: i-Pr₂EtN / acetonitrile / a) from -10 deg C to -5 deg C, 1 h, b) from 20 deg C to 25 deg C, 4 h

With hydrogenchloride; sodium hydroxide; ammonia; hydrogen; sodium methylate; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

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

Reference yield:

(2S,4R)-4-t-butyldimethylsilyloxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (117811-69-5) → (4R,5S,6S)-3-[(3S,5S)-5-Carbamoylmethoxymethyl-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (199998-96-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 48 percent / NaBH₄ / ethanol / 16 h / Ambient temperature

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

3: aq. NaOH / tetrahydrofuran / 2 h

4: 94 percent / NaH / tetrahydrofuran / 3 h / Ambient temperature

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

6: 4N aq. NaOH / tetrahydrofuran; H₂O / 2 h

7: 75 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

8: Et₃N / tetrahydrofuran / 0.5 h / -10 - -5 °C

9: NH₃ / tetrahydrofuran / 0.5 h / 0 °C

10: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, 90 deg C, 3 h

11: NaOMe / methanol / 1 h / -10 - -5 °C

12: i-Pr₂EtN / acetonitrile / a) from -10 deg C to -5 deg C, 1 h, b) from 20 deg C to 25 deg C, 4 h

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; ammonia; hydrogen; sodium methylate; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile;

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

upstream raw materials:

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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

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

(6S,8R)-8-t-butyldimethylsilyloxy-2-oxo-1-aza-4-oxabicyclo[4.3.0]nonane

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