(S)-4-Benzyl-3-[(4S,5R)-5-(4-fluoro-3-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-3-[(4S,5R)-5-(4-fluoro-3-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one
• CAS No.: 171738-37-7
• Molecular Formula: C₂₀H₁₆FN₃O₆S
• Molecular Weight: 445.428

Synonyms:(S)-4-Benzyl-3-[(4S,5R)-5-(4-fluoro-3-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one

Chemical Property of (S)-4-Benzyl-3-[(4S,5R)-5-(4-fluoro-3-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-Benzyl-3-[(4S,5R)-5-(4-fluoro-3-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one

There total 1 articles about (S)-4-Benzyl-3-[(4S,5R)-5-(4-fluoro-3-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-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:

4-fluoro-3-nitrobenzaldehyde (42564-51-2) + (4S)-3-(isothiocyanoacetyl)-4-(phenylmethyl)-2-oxazolidinone (104324-18-7) → (S)-4-Benzyl-3-[(4S,5R)-5-(4-fluoro-3-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one (171738-37-7)

Guidance literature:

With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate; Multistep reaction; 1.) THF, -78 deg C;

DOI:10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

Reference yield:

(S)-4-Benzyl-3-[(4S,5R)-5-(4-fluoro-3-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one (171738-37-7) → C58H53N5O11

Guidance literature:

Multi-step reaction with 28 steps

1: DMAP / CH₂Cl₂

2: HCO₂H, H₂O₂ / H₂O

3: LiOOH / -10 °C

4: EDCI*HCl, HOBt / tetrahydrofuran / 0 °C

5: LiOH / methanol; H₂O

6: TFA, Me₂S / CH₂Cl₂ / 0 °C

7: EDCI*HCl, HOBt / tetrahydrofuran / 0 °C

8: TFA, Me₂S / CH₂Cl₂ / 0 °C

9: 2,6-lutidine / CH₂Cl₂ / Ambient temperature

10: 65 percent / VOF₃, BF₃*Et₂O, AgBF₄ / trifluoroacetic acid; CH₂Cl₂ / 0 °C

11: NaHCO₃, H₂O / methanol / Ambient temperature

12: N-methylmorpholine / ethyl acetate / 0.5 h / -10 - -5 °C

13: ethyl acetate; dimethylformamide / 2 h / -20 - 20 °C

14: 85 percent / TBAF / CH₂Cl₂ / 0.25 h / 0 °C

15: Na₂CO₃ / dimethylsulfoxide / 66 h / Ambient temperature

16: 1 h

17: 74 percent / Zn, HOAc / ethanol / 40 °C

18: NaNO₂, H₃PO₂, H₂O / Cu₂O / tetrahydrofuran

19: Et₃N, HCO₂H / 2>*CH₂Cl₂ / dimethylformamide

20: Et₃N / tetrahydrofuran / Ambient temperature

21: TFA, Me₂S / CH₂Cl₂

22: 2,6-lutidine / CH₂Cl₂

23: 1.) AlBr₃, EtSH / 1.) CH₂Cl₂, 2.) MeOH

24: Cs₂CO₃, Bu₄NI / dimethylformamide

25: LiSEt / tetrahydrofuran

26: Cs₂CO₃ / dimethylformamide

27: LDA / tetrahydrofuran

28: LiOH, H₂O / tetrahydrofuran; methanol

With 4-methyl-morpholine; 2,6-dimethylpyridine; dmap; lithium hydroxide; silver tetrafluoroborate; formic acid; aluminum tri-bromide; vanadium(V) oxytrifluoride; lithium hydroperoxide; dimethylsulfide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; hypophosphorous acid; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; sodium carbonate; lithium thioethoxide; benzotriazol-1-ol; caesium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; ethanethiol; zinc; lithium diisopropyl amide; sodium nitrite; copper(I) oxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

Reference yield:

(S)-4-Benzyl-3-[(4S,5R)-5-(4-fluoro-3-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one (171738-37-7) → C58H50F3N5O14S

Guidance literature:

Multi-step reaction with 25 steps

1: DMAP / CH₂Cl₂

2: HCO₂H, H₂O₂ / H₂O

3: LiOOH / -10 °C

4: EDCI*HCl, HOBt / tetrahydrofuran / 0 °C

5: LiOH / methanol; H₂O

6: TFA, Me₂S / CH₂Cl₂ / 0 °C

7: EDCI*HCl, HOBt / tetrahydrofuran / 0 °C

8: TFA, Me₂S / CH₂Cl₂ / 0 °C

9: 2,6-lutidine / CH₂Cl₂ / Ambient temperature

10: 65 percent / VOF₃, BF₃*Et₂O, AgBF₄ / trifluoroacetic acid; CH₂Cl₂ / 0 °C

11: NaHCO₃, H₂O / methanol / Ambient temperature

12: N-methylmorpholine / ethyl acetate / 0.5 h / -10 - -5 °C

13: ethyl acetate; dimethylformamide / 2 h / -20 - 20 °C

14: 85 percent / TBAF / CH₂Cl₂ / 0.25 h / 0 °C

15: Na₂CO₃ / dimethylsulfoxide / 66 h / Ambient temperature

16: 1 h

17: 74 percent / Zn, HOAc / ethanol / 40 °C

18: NaNO₂, H₃PO₂, H₂O / Cu₂O / tetrahydrofuran

19: Et₃N, HCO₂H / 2>*CH₂Cl₂ / dimethylformamide

20: Et₃N / tetrahydrofuran / Ambient temperature

21: TFA, Me₂S / CH₂Cl₂

22: 2,6-lutidine / CH₂Cl₂

23: 1.) AlBr₃, EtSH / 1.) CH₂Cl₂, 2.) MeOH

24: Cs₂CO₃, Bu₄NI / dimethylformamide

25: LiSEt / tetrahydrofuran

With 4-methyl-morpholine; 2,6-dimethylpyridine; dmap; lithium hydroxide; silver tetrafluoroborate; formic acid; aluminum tri-bromide; vanadium(V) oxytrifluoride; lithium hydroperoxide; dimethylsulfide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; hypophosphorous acid; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; sodium carbonate; lithium thioethoxide; benzotriazol-1-ol; caesium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; ethanethiol; zinc; sodium nitrite; copper(I) oxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

upstream raw materials:

4-fluoro-3-nitrobenzaldehyde

(4S)-3-(isothiocyanoacetyl)-4-(phenylmethyl)-2-oxazolidinone

Downstream raw materials:

(4S,5R)-5-(4-Fluoro-3-nitro-phenyl)-2-oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester

(4S,5R)-4-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-(4-fluoro-3-nitro-phenyl)-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester

(4S,5R)-4-{[(S)-(3,5-Dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-5-(4-fluoro-3-nitro-phenyl)-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester

[(1S,2R)-1-{[(S)-(3,5-Dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester

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