(4R,5S,6S)-3-[(3S,5S)-5-(2,4-Dioxo-imidazolidin-1-ylmethyl)-1-(4-methoxy-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-methoxy-benzyl ester

Base Information

Chemical Name:(4R,5S,6S)-3-[(3S,5S)-5-(2,4-Dioxo-imidazolidin-1-ylmethyl)-1-(4-methoxy-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-methoxy-benzyl ester
CAS No.:175846-31-8
Molecular Formula:C₃₅H₄₀N₄O₁₀S
Molecular Weight:708.789
Hs Code.:

(4R,5S,6S)-3-[(3S,5S)-5-(2,4-Dioxo-imidazolidin-1-ylmethyl)-1-(4-methoxy-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-methoxy-benzyl ester

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Chemical Property of (4R,5S,6S)-3-[(3S,5S)-5-(2,4-Dioxo-imidazolidin-1-ylmethyl)-1-(4-methoxy-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-methoxy-benzyl ester

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Technology Process of (4R,5S,6S)-3-[(3S,5S)-5-(2,4-Dioxo-imidazolidin-1-ylmethyl)-1-(4-methoxy-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-methoxy-benzyl ester

There total 9 articles about (4R,5S,6S)-3-[(3S,5S)-5-(2,4-Dioxo-imidazolidin-1-ylmethyl)-1-(4-methoxy-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-methoxy-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:

: 1499-56-5,775275-31-5,790644-51-8,754962-86-2
(R)-4-hydroxy-L-proline ethyl ester

: 175846-31-8
(4R,5S,6S)-3-[(3S,5S)-5-(2,4-Dioxo-imidazolidin-1-ylmethyl)-1-(4-methoxy-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-methoxy-benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 32.48 g / triethylamine / methanol / 0.33 h

2: 98 percent / triethylamine / CH₂Cl₂ / 0.25 h / -30 °C

3: 1) sodium hydride / 1) DMF, room temperature, 1 h, 2) 60 deg C, 30 min

4: 68 percent / LiBH₄ / tetrahydrofuran / 0.5 h / 60 °C

5: 87.4 percent / triethylamine / CH₂Cl₂ / 0.33 h / -30 °C

6: 1) NaH / 1) DMF, room temperature, 10 min, 2) 80 deg C, 3 h

7: 1) AgNO₃, pyridine, 2) H₂S / 1) MeOH, CH₂Cl₂, H₂O, room temperature, 10 min

8: diisopropylethylamine / acetonitrile / 4.5 h

With pyridine; lithium borohydride; hydrogen sulfide; sodium hydride; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.7164/antibiotics.49.199

Reference yield:

: 104773-44-6
(2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester

: 175846-31-8
(4R,5S,6S)-3-[(3S,5S)-5-(2,4-Dioxo-imidazolidin-1-ylmethyl)-1-(4-methoxy-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-methoxy-benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / triethylamine / CH₂Cl₂ / 0.25 h / -30 °C

2: 1) sodium hydride / 1) DMF, room temperature, 1 h, 2) 60 deg C, 30 min

3: 68 percent / LiBH₄ / tetrahydrofuran / 0.5 h / 60 °C

4: 87.4 percent / triethylamine / CH₂Cl₂ / 0.33 h / -30 °C

5: 1) NaH / 1) DMF, room temperature, 10 min, 2) 80 deg C, 3 h

6: 1) AgNO₃, pyridine, 2) H₂S / 1) MeOH, CH₂Cl₂, H₂O, room temperature, 10 min

7: diisopropylethylamine / acetonitrile / 4.5 h

With pyridine; lithium borohydride; hydrogen sulfide; sodium hydride; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.7164/antibiotics.49.199

Reference yield:

: 148016-87-9
(2S,4R)-1-p-methoxybenzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylic acid methyl ester

: 175846-31-8
(4R,5S,6S)-3-[(3S,5S)-5-(2,4-Dioxo-imidazolidin-1-ylmethyl)-1-(4-methoxy-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-methoxy-benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1) sodium hydride / 1) DMF, room temperature, 1 h, 2) 60 deg C, 30 min

2: 68 percent / LiBH₄ / tetrahydrofuran / 0.5 h / 60 °C

3: 87.4 percent / triethylamine / CH₂Cl₂ / 0.33 h / -30 °C

4: 1) NaH / 1) DMF, room temperature, 10 min, 2) 80 deg C, 3 h

5: 1) AgNO₃, pyridine, 2) H₂S / 1) MeOH, CH₂Cl₂, H₂O, room temperature, 10 min

6: diisopropylethylamine / acetonitrile / 4.5 h

With pyridine; lithium borohydride; hydrogen sulfide; sodium hydride; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.7164/antibiotics.49.199