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

Base Information

• Chemical Name: (S)-4-Benzyl-3-[(4S,5R)-5-(3-chloro-4-fluoro-5-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one
• CAS No.: 218902-07-9
• Molecular Formula: C₂₀H₁₅ClFN₃O₆S
• Molecular Weight: 479.873

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

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

There total 1 articles about (S)-4-Benzyl-3-[(4S,5R)-5-(3-chloro-4-fluoro-5-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:

(4S)-3-(isothiocyanoacetyl)-4-(phenylmethyl)-2-oxazolidinone (104324-18-7) + 3-chloro-4-fluoro-5-nitro-benzaldehyde → (S)-4-Benzyl-3-[(4S,5R)-5-(3-chloro-4-fluoro-5-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one (218902-07-9)

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-(3-chloro-4-fluoro-5-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one (218902-07-9) → C63H57ClF3N5O15S (218902-05-7)

Guidance literature:

Multi-step reaction with 23 steps

1: DMAP / CH₂Cl₂

2: HCO₂H, H₂O₂ / H₂O

3: LiOOH / -5 °C

4: EDCI*HCl, HOBt / CH₂Cl₂; dimethylformamide / 0 °C

5: Li₂CO₃ / methanol / Ambient temperature

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 / 144 h / Ambient temperature

12: HATU, HOAt, collidine / CH₂Cl₂; dimethylformamide / 16 h / -20 °C

13: 85 percent / HF*pyridine / tetrahydrofuran / 1 h / Ambient temperature

14: Na₂CO₃ / dimethylsulfoxide / 1.5 h / Ambient temperature

15: 1 h

16: Zn, HOAc / ethanol / 40 °C

17: NaNO₂, H₃PO₂, H₂O / Cu₂O / tetrahydrofuran / 1 h / 0 °C

18: 87 percent / Et₃N, HCO₂H / 2>*CH₂Cl₂ / dimethylformamide / 75 °C

19: Et₃N / tetrahydrofuran / Ambient temperature

20: TFA, Me₂S / CH₂Cl₂ / 0 °C

21: 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

22: 1.) AlBr₃, EtSH / 1.) CH₂Cl₂, 0 deg C, 2.) MeOH, 55 deg C, 24 h

23: Cs₂CO₃, Bu₄NI / dimethylformamide / 0 °C

With 2,6-dimethylpyridine; 2,3,5-trimethyl-pyridine; dmap; silver tetrafluoroborate; formic acid; 1-hydroxy-7-aza-benzotriazole; aluminum tri-bromide; vanadium(V) oxytrifluoride; lithium hydroperoxide; dimethylsulfide; boron trifluoride diethyl etherate; water; dihydrogen peroxide; hypophosphorous acid; tetra-(n-butyl)ammonium iodide; lithium carbonate; sodium hydrogencarbonate; sodium carbonate; benzotriazol-1-ol; caesium carbonate; pyridine hydrogenfluoride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; ethanethiol; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; zinc; sodium nitrite; copper(I) oxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; 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-(3-chloro-4-fluoro-5-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one (218902-07-9) → C58H52ClN5O11 (218901-90-7)

Guidance literature:

Multi-step reaction with 27 steps

1: DMAP / CH₂Cl₂

2: HCO₂H, H₂O₂ / H₂O

3: LiOOH / -5 °C

4: EDCI*HCl, HOBt / CH₂Cl₂; dimethylformamide / 0 °C

5: Li₂CO₃ / methanol / Ambient temperature

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 / 144 h / Ambient temperature

12: HATU, HOAt, collidine / CH₂Cl₂; dimethylformamide / 16 h / -20 °C

13: 85 percent / HF*pyridine / tetrahydrofuran / 1 h / Ambient temperature

14: Na₂CO₃ / dimethylsulfoxide / 1.5 h / Ambient temperature

15: 1 h

16: Zn, HOAc / ethanol / 40 °C

17: NaNO₂, H₃PO₂, H₂O / Cu₂O / tetrahydrofuran / 1 h / 0 °C

18: 87 percent / Et₃N, HCO₂H / 2>*CH₂Cl₂ / dimethylformamide / 75 °C

19: Et₃N / tetrahydrofuran / Ambient temperature

20: TFA, Me₂S / CH₂Cl₂ / 0 °C

21: 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

22: 1.) AlBr₃, EtSH / 1.) CH₂Cl₂, 0 deg C, 2.) MeOH, 55 deg C, 24 h

23: Cs₂CO₃, Bu₄NI / dimethylformamide / 0 °C

24: LiSEt / tetrahydrofuran / 0 °C

25: Cs₂CO₃ / dimethylformamide / 0 °C

26: LDA / tetrahydrofuran / -78 °C

27: LiOH, H₂O / tetrahydrofuran; methanol / 0 °C

With 2,6-dimethylpyridine; 2,3,5-trimethyl-pyridine; dmap; lithium hydroxide; silver tetrafluoroborate; formic acid; 1-hydroxy-7-aza-benzotriazole; aluminum tri-bromide; vanadium(V) oxytrifluoride; lithium hydroperoxide; dimethylsulfide; boron trifluoride diethyl etherate; water; dihydrogen peroxide; hypophosphorous acid; tetra-(n-butyl)ammonium iodide; lithium carbonate; sodium hydrogencarbonate; sodium carbonate; lithium thioethoxide; benzotriazol-1-ol; caesium carbonate; pyridine hydrogenfluoride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; ethanethiol; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 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; 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:

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

Downstream raw materials:

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

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

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

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