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

Base Information

• Chemical Name: 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
• CAS No.: 120378-50-9
• Molecular Formula: C₂₇H₃₁N₆O₈S*Na
• Molecular Weight: 622.634

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 18 articles about 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 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) → 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 (120378-50-9,120378-54-3,120420-27-1)

Guidance literature:

Multi-step reaction with 19 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.,

18: H₂ / 10 percent Pd/C / ethyl acetate / 2 h / Ambient temperature; phosphate buffer, pH 7

19: ethyl acetate; tetrahydrofuran; various solvent(s) / 2 h / Ambient temperature

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:

(S)-2-Benzyloxycarbonylamino-4-imidazol-1-yl-4-oxo-butyric acid benzyl ester → 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 (120378-50-9,120378-54-3,120420-27-1)

Guidance literature:

Multi-step reaction with 18 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.,

17: H₂ / 10 percent Pd/C / ethyl acetate / 2 h / Ambient temperature; phosphate buffer, pH 7

18: ethyl acetate; tetrahydrofuran; various solvent(s) / 2 h / Ambient temperature

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:

dibenzyl <5S>-5-benzyloxycarbonylamino-3-oxohexane-1,6-dioate (120378-62-3) → 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 (120378-50-9,120378-54-3,120420-27-1)

Guidance literature:

Multi-step reaction with 17 steps

1: toluene / 0.5 h / Heating

2: 1 h / 150 - 160 °C / 20 Torr

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

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

5: NaHCO₃ / H₂O / 18 h / Ambient temperature

6: K₂CO₃ / dimethylformamide / 18 h / Ambient temperature

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

8: Et₃N / H₂O; tetrahydrofuran

9: tetrahydrofuran / 2 h / Ambient temperature

10: tetrahydrofuran / 18 h / Ambient temperature

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

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

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

14: THF / CH₂Cl₂ / 2 h / 5 °C

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

16: H₂ / 10 percent Pd/C / ethyl acetate / 2 h / Ambient temperature; phosphate buffer, pH 7

17: ethyl acetate; tetrahydrofuran; various solvent(s) / 2 h / Ambient temperature

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:

acetic anhydride

(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

Z-Asp-OBn

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

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