N-(ISOTHIOCYANOACETYL)-(4R)-BENZYL-2-OXAZOLIDINONE

Base Information

• Chemical Name: N-(ISOTHIOCYANOACETYL)-(4R)-BENZYL-2-OXAZOLIDINONE
• CAS No.: 104324-18-7
• Molecular Formula: C13H12 N2 O3 S
• Molecular Weight: 276.316
• Hs Code.: 2934999090
• Mol file: 104324-18-7.mol

Synonyms:2-Oxazolidinone,3-(isothiocyanatoacetyl)-4-(phenylmethyl)-, (4S)- (9CI); 2-Oxazolidinone,3-(isothiocyanatoacetyl)-4-(phenylmethyl)-, (S)-

Chemical Property of N-(ISOTHIOCYANOACETYL)-(4R)-BENZYL-2-OXAZOLIDINONE

Chemical Property:

• PSA: 91.06000
• LogP: 1.61720

Purity/Quality:

95% ^*data from raw suppliers

N-(ISOTHIOCYANOACETYL)-(4S)-BENZYL-2-OXAZOLIDINONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(ISOTHIOCYANOACETYL)-(4R)-BENZYL-2-OXAZOLIDINONE

There total 6 articles about N-(ISOTHIOCYANOACETYL)-(4R)-BENZYL-2-OXAZOLIDINONE 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: 79.0%

carbon disulfide (75-15-0,12122-00-8) + (4S)-(+)-3-(azidoacetyl)-4-(phenylmethyl)-2-oxazolidinone (104324-17-6) → (4S)-3-(isothiocyanoacetyl)-4-(phenylmethyl)-2-oxazolidinone (104324-18-7)

Guidance literature:

With triphenylphosphine;

DOI:10.1016/0040-4039(95)01409-B

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (4S)-3-(isothiocyanoacetyl)-4-(phenylmethyl)-2-oxazolidinone (104324-18-7)

Guidance literature:

Multi-step reaction with 5 steps

2: 84 percent / potassium carbonate / 2 h / 135 - 140 °C

3: n-butyllithium / hexane; tetrahydrofuran / 15 min, -78 deg C; 15 min, r.t.

4: sodium azide / tetrabutylammonium hydrogen sulfate / H₂O; CH₂Cl₂ / 1 h / Ambient temperature

5: 1.) hydrogen, 70percent perchloric acid; 2.) sodium bicarbonate / 1.) 10percent palladium on carbon / 1.) water, methanol, 1 atm, overnight; 2.) water, chloroform, 10 min, r.t.

With n-butyllithium; sodium azide; perchloric acid; hydrogen; sodium hydrogencarbonate; potassium carbonate; palladium on activated charcoal; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1021/ja00281a049

Reference yield:

L-Phenylalaninol (3182-95-4) → (4S)-3-(isothiocyanoacetyl)-4-(phenylmethyl)-2-oxazolidinone (104324-18-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / potassium carbonate / 2 h / 135 - 140 °C

2: n-butyllithium / hexane; tetrahydrofuran / 15 min, -78 deg C; 15 min, r.t.

3: sodium azide / tetrabutylammonium hydrogen sulfate / H₂O; CH₂Cl₂ / 1 h / Ambient temperature

4: 1.) hydrogen, 70percent perchloric acid; 2.) sodium bicarbonate / 1.) 10percent palladium on carbon / 1.) water, methanol, 1 atm, overnight; 2.) water, chloroform, 10 min, r.t.

With n-butyllithium; sodium azide; perchloric acid; hydrogen; sodium hydrogencarbonate; potassium carbonate; palladium on activated charcoal; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1021/ja00281a049

upstream raw materials:

thiophosgene

(4S)-(+)-3-(azidoacetyl)-4-(phenylmethyl)-2-oxazolidinone

carbon disulfide

L-phenylalanine

Downstream raw materials:

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

(4S)-3-<((4'S,5'R)-5'-methyl-2'-thioxo-4'-oxazolidinyl)carbonyl>-4-(phenylmethyl)-2-oxazolidinone

(4S)-4-benzyl-3-[(4S,5R)-1-[5-[3,4-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidin-4-yl]methanoyl]oxazolidin-2-one

(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