3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfamoyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid

Base Information

Chemical Name:3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfamoyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid
CAS No.:153785-34-3
Molecular Formula:C₂₀H₂₂N₄O₇S
Molecular Weight:462.483
Hs Code.:

Synonyms:3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfamoyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid

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Chemical Property of 3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfamoyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid

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Technology Process of 3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfamoyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid

There total 5 articles about 3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfamoyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid 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: 52.4%

: 153785-20-7
3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfamoyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid 4-nitro-benzyl ester

: 153785-34-3
3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfamoyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; under 1900 Torr;
DOI:10.1016/S0040-4020(01)80182-4

Reference yield:

: 29124-80-9
1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanic acid 4-nitro-benzyl ester

: 153785-34-3
3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfamoyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: N-chlorosuccinimide, calcium oxide / toluene / 1.5 h / Heating

2: toluene / 2 h

3: 91 percent / triethylamine / CH₂Cl₂ / 2 h / Ambient temperature

4: formic acid, 30percent aqueous H₂O₂ / CH₂Cl₂ / Ambient temperature

5: 52.4 percent / H₂ / 10percent Pd/C / methanol / 1900 Torr

With N-chloro-succinimide; formic acid; hydrogen; dihydrogen peroxide; triethylamine; calcium oxide; palladium on activated charcoal; In methanol; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)80182-4

Reference yield:

: 76085-04-6
(R)-2-((2R,3R)-2-Chlorosulfinyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-3-methyl-but-3-enoic acid 4-nitro-benzyl ester

: 153785-34-3
3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfamoyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid

Guidance literature:: Multi-step reaction with 4 steps

1: toluene / 2 h

2: 91 percent / triethylamine / CH₂Cl₂ / 2 h / Ambient temperature

3: formic acid, 30percent aqueous H₂O₂ / CH₂Cl₂ / Ambient temperature

4: 52.4 percent / H₂ / 10percent Pd/C / methanol / 1900 Torr

With formic acid; hydrogen; dihydrogen peroxide; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)80182-4