3-[(1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropanecarbonyl]-4(S)-phenyloxazolidin-2-one

Base Information

Chemical Name:3-[(1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropanecarbonyl]-4(S)-phenyloxazolidin-2-one
CAS No.:1355996-23-4
Molecular Formula:C₂₅H₂₂N₂O₄
Molecular Weight:414.461
Hs Code.:

Synonyms:

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Chemical Property of 3-[(1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropanecarbonyl]-4(S)-phenyloxazolidin-2-one

Chemical Property:

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Technology Process of 3-[(1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropanecarbonyl]-4(S)-phenyloxazolidin-2-one

There total 12 articles about 3-[(1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropanecarbonyl]-4(S)-phenyloxazolidin-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:

: C₁₆H₁₄ClNO₂

: 99395-88-7,7480-32-2
(S)-4-phenyl-2-oxazolidinone

: 1355996-23-4
3-[(1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropanecarbonyl]-4(S)-phenyloxazolidin-2-one

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1021/jm201157c

Reference yield:

: 130722-95-1
3-(benzyloxy)-5-bromopyridine

: 1355996-23-4
3-[(1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropanecarbonyl]-4(S)-phenyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: phenyl carbamate; palladium diacetate; potassium carbonate / N,N-dimethyl-formamide / 4 h / 130 °C / Inert atmosphere

2.1: water; sodium hydroxide / tetrahydrofuran; methanol / 4 h / 20 °C

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere

4.1: sodium hydride / dimethyl sulfoxide / 1.17 h / Inert atmosphere

4.2: 2 h / 20 °C / Inert atmosphere

5.1: tetrahydrofuran / 2 h / -78 - -20 °C / Inert atmosphere

6.1: sodium tetrahydroborate / methanol / 3.25 h / 0 - 20 °C / Inert atmosphere

7.1: Chiralpak AD-H / ethanol / Resolution of racemate

8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.92 h / Inert atmosphere; Cooling with acetone-dry ice

8.2: 0.75 h / Inert atmosphere

9.1: sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0 - 20 °C

10.1: pivaloyl chloride; triethylamine / tetrahydrofuran / 0.25 h / -78 - 0 °C / Inert atmosphere

11.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 20 °C / Inert atmosphere

With dmap; sodium chlorite; sodium tetrahydroborate; potassium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; phenyl carbamate; water; palladium diacetate; pivaloyl chloride; sodium hydride; potassium carbonate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Heck reaction / 4.1: Corey-Chaykowsky cyclopropanation reaction / 4.2: Corey-Chaykowsky cyclopropanation reaction / 8.1: Swern oxidation;
DOI:10.1021/jm201157c

Reference yield:

: 1222136-50-6
trans-3-[5-(benzyloxy)-3-pyridyl]acrylic acid n-butyl ester

: 1355996-23-4
3-[(1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropanecarbonyl]-4(S)-phenyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: water; sodium hydroxide / tetrahydrofuran; methanol / 4 h / 20 °C

2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere

3.1: sodium hydride / dimethyl sulfoxide / 1.17 h / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

4.1: tetrahydrofuran / 2 h / -78 - -20 °C / Inert atmosphere

5.1: sodium tetrahydroborate / methanol / 3.25 h / 0 - 20 °C / Inert atmosphere

6.1: Chiralpak AD-H / ethanol / Resolution of racemate

7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.92 h / Inert atmosphere; Cooling with acetone-dry ice

7.2: 0.75 h / Inert atmosphere

8.1: sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0 - 20 °C

9.1: pivaloyl chloride; triethylamine / tetrahydrofuran / 0.25 h / -78 - 0 °C / Inert atmosphere

10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 20 °C / Inert atmosphere

With dmap; sodium chlorite; sodium tetrahydroborate; potassium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; water; pivaloyl chloride; sodium hydride; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; 3.1: Corey-Chaykowsky cyclopropanation reaction / 3.2: Corey-Chaykowsky cyclopropanation reaction / 7.1: Swern oxidation;
DOI:10.1021/jm201157c