benzyl (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

Base Information

Chemical Name:benzyl (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate
CAS No.:865704-61-6
Molecular Formula:C₂₃H₂₄N₂O₅
Molecular Weight:408.454
Hs Code.:

Synonyms:benzyl (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

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Chemical Property of benzyl (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

Chemical Property:

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MSDS Files:: SDS file from LookChem

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Technology Process of benzyl (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

There total 10 articles about benzyl (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate 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: 68.0%

: 865704-59-2
(3S)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-({[(benzyloxy)carbonyl]amino}methyl)-4-oxobutanoic acid

: 865704-61-6
benzyl (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

Guidance literature:: With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃;
DOI:10.1055/s-2005-865362

Reference yield:

: 865704-45-6
4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid

: 865704-61-6
benzyl (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 50 percent / P₂O₅ / CHCl₃ / 60 h / 20 °C

2.1: NaI; NaHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: 60 percent / tetrahydrofuran / 4 h / -95 - -75 °C

3.1: 100 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 760 Torr

4.1: Et₃N / tetrahydrofuran / 0.5 h / -15 - 20 °C

5.1: aq. NaN₃ / tetrahydrofuran / 1 h / 0 °C

6.1: toluene / Heating

7.1: 0.82 g / toluene / Heating

8.1: 96 percent / TFA / CH₂Cl₂ / 20 °C

9.1: 68 percent / BH₃*Me₂S / tetrahydrofuran / 20 °C

With sodium azide; dimethylsulfide borane complex; hydrogen; sodium hexamethyldisilazane; phosphorus pentoxide; triethylamine; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; toluene; 6.1: Curtius rearrangement;
DOI:10.1055/s-2005-865362

Reference yield:

: 865704-46-7
tert-butyl 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoate

: 865704-61-6
benzyl (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaI; NaHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: 60 percent / tetrahydrofuran / 4 h / -95 - -75 °C

2.1: 100 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 760 Torr

3.1: Et₃N / tetrahydrofuran / 0.5 h / -15 - 20 °C

4.1: aq. NaN₃ / tetrahydrofuran / 1 h / 0 °C

5.1: toluene / Heating

6.1: 0.82 g / toluene / Heating

7.1: 96 percent / TFA / CH₂Cl₂ / 20 °C

8.1: 68 percent / BH₃*Me₂S / tetrahydrofuran / 20 °C

With sodium azide; dimethylsulfide borane complex; hydrogen; sodium hexamethyldisilazane; triethylamine; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 5.1: Curtius rearrangement;
DOI:10.1055/s-2005-865362