(6R,12S)-1-aza-3-(pyroglutamylamino)-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

Base Information

• Chemical Name: (6R,12S)-1-aza-3-(pyroglutamylamino)-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene
• CAS No.: 325460-70-6
• Molecular Formula: C₂₁H₂₃N₃O₅
• Molecular Weight: 397.431
• Mol file: 325460-70-6.mol

Synonyms:(6R,12S)-1-aza-3-(pyroglutamylamino)-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

Chemical Property of (6R,12S)-1-aza-3-(pyroglutamylamino)-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,12S)-1-aza-3-(pyroglutamylamino)-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

There total 16 articles about (6R,12S)-1-aza-3-(pyroglutamylamino)-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene 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:

(R)-N-(benzoyloxycarbonyl)-allylproline methyl ester (157662-40-3) → (6R,12S)-1-aza-3-(pyroglutamylamino)-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene (325460-70-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: O₃ / CH₂Cl₂ / 1.25 h / -78 °C

2.1: 9.96 g / CH₂Cl₂ / -78 - 20 °C

3.1: 61 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / -78 - -20 °C

4.1: H₂ / Pd/BaSO₄ / methanol

5.1: 2.4 g / Et₃N / toluene / 21 h / Heating

6.1: 93 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

7.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

8.1: KHMDS / toluene; CH₂Cl₂ / 1 h / -78 °C

8.2: 72 percent / O₂ / CH₂Cl₂; toluene / 0.02 h / -78 °C

9.1: 69 percent / NH₃ / methanol / 144 h / 50 °C

10.1: 0.196 g / tetrahydrofuran / -20 - 20 °C

11.1: 86 percent / aq. H₂SO₄ / tetrahydrofuran

12.1: 46 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h

13.1: PDC / dimethylformamide / 21 h

14.1: 4 mg / dimethylformamide / 0.25 h

With 2,6-dimethylpyridine; dipyridinium dichromate; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; ammonia; hydrogen; potassium hexamethylsilazane; ozone; triethylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: ozonolysis / 2.1: Wittig reaction / 3.1: Addition / 4.1: Hydrogenolysis / 5.1: cyclocondensation / 6.1: Reduction / 7.1: Condensation / 8.1: deprotonation / 8.2: Oxidation / 9.1: Substitution / 10.1: Condensation / 11.1: Hydrolysis / 12.1: Oxidation / 13.1: Oxidation / 14.1: Esterification;

DOI:10.1016/S0040-4020(00)00886-3

Reference yield:

(R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester (157662-41-4) → (6R,12S)-1-aza-3-(pyroglutamylamino)-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene (325460-70-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 9.96 g / CH₂Cl₂ / -78 - 20 °C

2.1: 61 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / -78 - -20 °C

3.1: H₂ / Pd/BaSO₄ / methanol

4.1: 2.4 g / Et₃N / toluene / 21 h / Heating

5.1: 93 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

6.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

7.1: KHMDS / toluene; CH₂Cl₂ / 1 h / -78 °C

7.2: 72 percent / O₂ / CH₂Cl₂; toluene / 0.02 h / -78 °C

8.1: 69 percent / NH₃ / methanol / 144 h / 50 °C

9.1: 0.196 g / tetrahydrofuran / -20 - 20 °C

10.1: 86 percent / aq. H₂SO₄ / tetrahydrofuran

11.1: 46 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h

12.1: PDC / dimethylformamide / 21 h

13.1: 4 mg / dimethylformamide / 0.25 h

With 2,6-dimethylpyridine; dipyridinium dichromate; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; ammonia; hydrogen; potassium hexamethylsilazane; triethylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Wittig reaction / 2.1: Addition / 3.1: Hydrogenolysis / 4.1: cyclocondensation / 5.1: Reduction / 6.1: Condensation / 7.1: deprotonation / 7.2: Oxidation / 8.1: Substitution / 9.1: Condensation / 10.1: Hydrolysis / 11.1: Oxidation / 12.1: Oxidation / 13.1: Esterification;

DOI:10.1016/S0040-4020(00)00886-3

Reference yield:

(2R)-N-(benzyloxycarbonyl)-2-[(E)-3'-(carbomethoxy)prop-2'-enyl]proline methyl ester (325460-62-6) → (6R,12S)-1-aza-3-(pyroglutamylamino)-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene (325460-70-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 61 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / -78 - -20 °C

2.1: H₂ / Pd/BaSO₄ / methanol

3.1: 2.4 g / Et₃N / toluene / 21 h / Heating

4.1: 93 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

5.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

6.1: KHMDS / toluene; CH₂Cl₂ / 1 h / -78 °C

6.2: 72 percent / O₂ / CH₂Cl₂; toluene / 0.02 h / -78 °C

7.1: 69 percent / NH₃ / methanol / 144 h / 50 °C

8.1: 0.196 g / tetrahydrofuran / -20 - 20 °C

9.1: 86 percent / aq. H₂SO₄ / tetrahydrofuran

10.1: 46 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h

11.1: PDC / dimethylformamide / 21 h

12.1: 4 mg / dimethylformamide / 0.25 h

With 2,6-dimethylpyridine; dipyridinium dichromate; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; ammonia; hydrogen; potassium hexamethylsilazane; triethylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Addition / 2.1: Hydrogenolysis / 3.1: cyclocondensation / 4.1: Reduction / 5.1: Condensation / 6.1: deprotonation / 6.2: Oxidation / 7.1: Substitution / 8.1: Condensation / 9.1: Hydrolysis / 10.1: Oxidation / 11.1: Oxidation / 12.1: Esterification;

DOI:10.1016/S0040-4020(00)00886-3

upstream raw materials:

methanol

(R)-N-(benzoyloxycarbonyl)-allylproline methyl ester

(R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester

L-Pyroglutamic acid