(5S,7S)-7-<(2R)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-phenylacetamido>-2-(4-nitrobenzyloxycarbonyl)-3-<2-(4-nitrobenzyloxycarbonylamino)ethylthio>-1-azabicyclo-<3.3.O>oct-2-en-8-one

Base Information

• Chemical Name: (5S,7S)-7-<(2R)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-phenylacetamido>-2-(4-nitrobenzyloxycarbonyl)-3-<2-(4-nitrobenzyloxycarbonylamino)ethylthio>-1-azabicyclo-<3.3.O>oct-2-en-8-one
• CAS No.: 120397-48-0
• Molecular Formula: C₄₀H₄₀N₈O₁₃S
• Molecular Weight: 872.869

Synonyms:

Chemical Property of (5S,7S)-7-<(2R)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-phenylacetamido>-2-(4-nitrobenzyloxycarbonyl)-3-<2-(4-nitrobenzyloxycarbonylamino)ethylthio>-1-azabicyclo-<3.3.O>oct-2-en-8-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,7S)-7-<(2R)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-phenylacetamido>-2-(4-nitrobenzyloxycarbonyl)-3-<2-(4-nitrobenzyloxycarbonylamino)ethylthio>-1-azabicyclo-<3.3.O>oct-2-en-8-one

There total 32 articles about (5S,7S)-7-<(2R)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-phenylacetamido>-2-(4-nitrobenzyloxycarbonyl)-3-<2-(4-nitrobenzyloxycarbonylamino)ethylthio>-1-azabicyclo-<3.3.O>oct-2-en-8-one 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:

Z-Asp-OBn (4779-31-1) → (5S,7S)-7-<(2R)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-phenylacetamido>-2-(4-nitrobenzyloxycarbonyl)-3-<2-(4-nitrobenzyloxycarbonylamino)ethylthio>-1-azabicyclo-<3.3.O>oct-2-en-8-one (120397-48-0,120420-26-0)

Guidance literature:

Multi-step reaction with 17 steps

1: tetrahydrofuran / 2 h / Ambient temperature

2: tetrahydrofuran / 16 h / Ambient temperature

3: toluene / 0.5 h / Heating

4: 1 h / 150 - 160 °C / 20 Torr

5: CAN / H₂O; acetone; methanol / 1.5 h / 5 °C

6: H₂ / 10 percent Pd/C / ethyl acetate; H₂O / 8 h / Ambient temperature

7: NaHCO₃ / H₂O / 18 h / Ambient temperature

8: K₂CO₃ / dimethylformamide / 18 h / Ambient temperature

9: H₂ / 10 percent Pd/C / ethyl acetate; H₂O

10: Et₃N / H₂O; tetrahydrofuran

11: tetrahydrofuran / 2 h / Ambient temperature

12: tetrahydrofuran / 18 h / Ambient temperature

13: Et₃N, p-Toz-N₃ / acetonitrile / 1 h / 5 °C

14: Rh₂(OAc)4 / tetrahydrofuran; benzene / 2 h / 80 - 90 °C

15: Et₃N, p-Toz-N₃ / acetonitrile / 1 h / 5 °C

16: THF / CH₂Cl₂ / 2 h / 5 °C

17: 1.) HOBt, DCC / 2.) THF, 4 h, room t.,

With tetrahydrofuran; 4-toluenesulfonyl azide; ammonium cerium(IV) nitrate; hydrogen; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; dirhodium tetraacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;

Reference yield:

Z-Asp-OBn (4779-31-1) → (5S,7S)-7-<(2R)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-phenylacetamido>-2-(4-nitrobenzyloxycarbonyl)-3-<2-(4-nitrobenzyloxycarbonylamino)ethylthio>-1-azabicyclo-<3.3.O>oct-2-en-8-one (120397-48-0,120420-26-0)

Guidance literature:

Multi-step reaction with 16 steps

1: tetrahydrofuran / 2 h / Ambient temperature

2: tetrahydrofuran / 16 h / Ambient temperature

3: toluene / 0.5 h / Heating

4: 1 h / 150 - 160 °C / 20 Torr

5: CAN / H₂O; acetone; methanol / 1.5 h / 5 °C

6: H₂ / 10 percent Pd/C / ethyl acetate; H₂O / 8 h / Ambient temperature

7: NaHCO₃ / H₂O / 18 h / Ambient temperature

8: H₂ / 10 percent Pd/C / methanol / 2 h / Ambient temperature

9: Et₃N / H₂O; tetrahydrofuran

10: tetrahydrofuran / 2 h / Ambient temperature

11: tetrahydrofuran / 18 h / Ambient temperature

12: Et₃N, p-Toz-N₃ / acetonitrile / 1 h / 5 °C

13: Rh₂(OAc)4 / tetrahydrofuran; benzene / 2 h / 80 - 90 °C

14: 1.) diphenylphosphoryl chloride, Prⁱ2NET / 1.) acetonitrile, 5 deg C, 30 min, 2.) 5 deg C, 18 h

15: TFA / CH₂Cl₂ / 2 h / 5 °C

16: 1.) HOBt, DCC / 2.) THF, 4 h, room t.,

With 4-toluenesulfonyl azide; ammonium cerium(IV) nitrate; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; Diphenylphosphinic chloride; dirhodium tetraacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile; benzene;

Reference yield:

(S)-2-Benzyloxycarbonylamino-4-imidazol-1-yl-4-oxo-butyric acid benzyl ester → (5S,7S)-7-<(2R)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-phenylacetamido>-2-(4-nitrobenzyloxycarbonyl)-3-<2-(4-nitrobenzyloxycarbonylamino)ethylthio>-1-azabicyclo-<3.3.O>oct-2-en-8-one (120397-48-0,120420-26-0)

Guidance literature:

Multi-step reaction with 16 steps

1: tetrahydrofuran / 16 h / Ambient temperature

2: toluene / 0.5 h / Heating

3: 1 h / 150 - 160 °C / 20 Torr

4: CAN / H₂O; acetone; methanol / 1.5 h / 5 °C

5: H₂ / 10 percent Pd/C / ethyl acetate; H₂O / 8 h / Ambient temperature

6: NaHCO₃ / H₂O / 18 h / Ambient temperature

7: K₂CO₃ / dimethylformamide / 18 h / Ambient temperature

8: H₂ / 10 percent Pd/C / ethyl acetate; H₂O

9: Et₃N / H₂O; tetrahydrofuran

10: tetrahydrofuran / 2 h / Ambient temperature

11: tetrahydrofuran / 18 h / Ambient temperature

12: Et₃N, p-Toz-N₃ / acetonitrile / 1 h / 5 °C

13: Rh₂(OAc)4 / tetrahydrofuran; benzene / 2 h / 80 - 90 °C

14: Et₃N, p-Toz-N₃ / acetonitrile / 1 h / 5 °C

15: THF / CH₂Cl₂ / 2 h / 5 °C

16: 1.) HOBt, DCC / 2.) THF, 4 h, room t.,

With tetrahydrofuran; 4-toluenesulfonyl azide; ammonium cerium(IV) nitrate; hydrogen; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; dirhodium tetraacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;

upstream raw materials:

2-(4-nitrobenzyloxycarbonylamino)ethanethiol

Z-Asp-OBn

dibenzyl <5S>-5-benzyloxycarbonylamino-3-oxohexane-1,6-dioate

(3S)-7-benzyloxycarbonylamino-5-(E)-benzyloxycarbonyl-methylidene-1-(2,4-dimetoxybenzyl)pyrrolidin-2-one

Downstream raw materials:

(5S,7S)-3-(2-aminoethylsulphonyl)-2-carboxy-7-<(2R)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-phenylacetamido>-1-azabicyclo<3.3.O>oct-2-en-8-one

sodium (5R,7S)-3-(-2-acetamidoethylthio)-7-<(2R)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-phenylacetamido>-8-oxo-1-azabicyclo<3.3.O>oct-2-ene-2-carboxylate

(6S,7aR)-2-(2-Amino-ethylsulfanyl)-6-{2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-2-phenyl-acetylamino}-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid

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