(R)-3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfinamoyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-but-3-enoic acid methyl ester

Base Information

• Chemical Name: (R)-3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfinamoyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-but-3-enoic acid methyl ester
• CAS No.: 153784-96-4
• Molecular Formula: C₂₁H₂₄N₄O₇S
• Molecular Weight: 476.51

Synonyms:(R)-3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfinamoyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-but-3-enoic acid methyl ester

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

Chemical Property:

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

There total 2 articles about (R)-3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfinamoyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-but-3-enoic acid methyl ester 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:

methyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide (10209-03-7) → (R)-3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfinamoyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-but-3-enoic acid methyl ester (153784-96-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: toluene / 2 h

With N-chloro-succinimide; calcium oxide; In toluene;

DOI:10.1016/S0040-4020(01)80182-4

Reference yield:

5-methylisoxazol-3-ylamine (1072-67-9) + (R)-2-[(2R,3R)-2-Chlorosulfinyl-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid methyl ester (153785-01-4) → (R)-3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfinamoyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-but-3-enoic acid methyl ester (153784-96-4)

Guidance literature:

In toluene; for 2h; Yield given;

DOI:10.1016/S0040-4020(01)80182-4

Reference yield: 80.4%

(R)-3-Methyl-2-[(2R,3R)-2-(5-methyl-isoxazol-3-ylsulfinamoyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-but-3-enoic acid methyl ester (153784-96-4) → (2R,3R) 1-(1'-methyloxycarbonyl-2'-methyl-prop-1'-enyl)-2-[(5'-methyl-isoxazol-3'-yl)-aminosulfinyl]-3-phenoxyacetamido-4-oxo-azetidine (153785-06-9)

Guidance literature:

With triethylamine; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80182-4

upstream raw materials:

5-methylisoxazol-3-ylamine

(R)-2-[(2R,3R)-2-Chlorosulfinyl-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid methyl ester

methyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide

Downstream raw materials:

(2R,3R) 1-(1'-methyloxycarbonyl-2'-methyl-prop-1'-enyl)-2-[(5'-methyl-isoxazol-3'-yl)-aminosulfinyl]-3-phenoxyacetamido-4-oxo-azetidine

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