(4S,5R)-5-(1,1-Dichloro-2-hydroxy-ethyl)-4-methoxy-1-(toluene-4-sulfonyl)-imidazolidin-2-one

Base Information

• Chemical Name: (4S,5R)-5-(1,1-Dichloro-2-hydroxy-ethyl)-4-methoxy-1-(toluene-4-sulfonyl)-imidazolidin-2-one
• CAS No.: 374934-58-4
• Molecular Formula: C₁₃H₁₆Cl₂N₂O₅S
• Molecular Weight: 383.252
• Mol file: 374934-58-4.mol

Synonyms:(4S,5R)-5-(1,1-Dichloro-2-hydroxy-ethyl)-4-methoxy-1-(toluene-4-sulfonyl)-imidazolidin-2-one

Chemical Property of (4S,5R)-5-(1,1-Dichloro-2-hydroxy-ethyl)-4-methoxy-1-(toluene-4-sulfonyl)-imidazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-5-(1,1-Dichloro-2-hydroxy-ethyl)-4-methoxy-1-(toluene-4-sulfonyl)-imidazolidin-2-one

There total 6 articles about (4S,5R)-5-(1,1-Dichloro-2-hydroxy-ethyl)-4-methoxy-1-(toluene-4-sulfonyl)-imidazolidin-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: 90.0%

C25H30Cl2N2O8S (374934-57-3) → (4S,5R)-5-(1,1-Dichloro-2-hydroxy-ethyl)-4-methoxy-1-(toluene-4-sulfonyl)-imidazolidin-2-one (374934-58-4)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; methanol; at 20 ℃;

DOI:10.1016/S0040-4039(01)01242-4

Reference yield:

Trichloro-acetic acid 2-[(1S,2R,4R)-1-(3-acetyl-2-oxo-2,3-dihydro-imidazole-1-carbonyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-yloxy]-ethyl ester (374934-54-0) → (4S,5R)-5-(1,1-Dichloro-2-hydroxy-ethyl)-4-methoxy-1-(toluene-4-sulfonyl)-imidazolidin-2-one (374934-58-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / ZnCl₂ / RuCl₂(PPh₃)3 / benzene / 1 h / Heating

2: 97 percent / 1 h / Heating

3: 78 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

4: 90 percent / LiBH₄ / methanol; tetrahydrofuran / 20 °C

With dmap; lithium borohydride; triethylamine; zinc(II) chloride; tris(triphenylphosphine)ruthenium(II) chloride; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4039(01)01242-4

Reference yield:

Trichloro-acetic acid 2-[(1S,2R,4R)-1-(3-benzoyl-2-oxo-2,3-dihydro-imidazole-1-carbonyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-yloxy]-ethyl ester (374934-70-0) → (4S,5R)-5-(1,1-Dichloro-2-hydroxy-ethyl)-4-methoxy-1-(toluene-4-sulfonyl)-imidazolidin-2-one (374934-58-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / La(OTf)3 / RuCl₂(PPh₃)3 / benzene / 1 h / Heating

2: 97 percent / 1 h / Heating

3: 78 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

4: 90 percent / LiBH₄ / methanol; tetrahydrofuran / 20 °C

With dmap; lithium borohydride; triethylamine; lanthanum(lll) triflate; tris(triphenylphosphine)ruthenium(II) chloride; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4039(01)01242-4

upstream raw materials:

C₂₅H₃₀Cl₂N₂O₈S

C₁₈H₂₄Cl₂N₂O₆

Trichloro-acetic acid 2-[(1S,2R,4R)-1-(3-acetyl-2-oxo-2,3-dihydro-imidazole-1-carbonyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-yloxy]-ethyl ester

C₁₉H₂₃Cl₃N₂O₆

Downstream raw materials:

(4S,5R)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-1,1-dichloro-ethyl]-4-isobutyl-1-(toluene-4-sulfonyl)-imidazolidin-2-one

Dichloro-[(4R,5S)-5-isobutyl-2-oxo-3-(toluene-4-sulfonyl)-imidazolidin-4-yl]-acetic acid methyl ester