3-Methyl-2-((2R,3R)-2-methylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-but-2-enoic acid methyl ester

Base Information

• Chemical Name: 3-Methyl-2-((2R,3R)-2-methylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-but-2-enoic acid methyl ester
• CAS No.: 55826-28-3
• Molecular Formula: C₁₈H₂₂N₂O₄S
• Molecular Weight: 362.45

Synonyms:3-Methyl-2-((2R,3R)-2-methylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-but-2-enoic acid methyl ester

Chemical Property of 3-Methyl-2-((2R,3R)-2-methylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-but-2-enoic acid methyl ester

Chemical Property:

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Technology Process of 3-Methyl-2-((2R,3R)-2-methylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-but-2-enoic acid methyl ester

There total 8 articles about 3-Methyl-2-((2R,3R)-2-methylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-but-2-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: 67.0%

2-((2R,3S)-3-Amino-2-methylsulfanyl-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid methyl ester (66530-14-1,79056-40-9) + phenylacetyl chloride (103-80-0) → 3-Methyl-2-((2R,3S)-2-methylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-but-2-enoic acid methyl ester (55826-28-3,55870-59-2,64838-98-8,64838-99-9,79056-39-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4020(01)88885-2

Reference yield: 43.9%

2-{(2R,3R)-2-[(2R,3R)-1-(1-Methoxycarbonyl-2-methyl-propenyl)-4-oxo-3-phenylacetylamino-azetidin-2-yldisulfanyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-3-methyl-but-2-enoic acid methyl ester (62284-27-9) + phosphorous acid trimethyl ester (121-45-9) → 3-Methyl-2-((2R,3R)-2-methylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-but-2-enoic acid methyl ester (55826-28-3)

Guidance literature:

In benzene; at 100 ℃; for 0.75h;

DOI:10.1248/cpb.31.1874

Reference yield:

3-Methyl-2-methylsulfanylmethyleneamino-but-2-enoic acid methyl ester (35859-85-9) → 3-Methyl-2-((2R,3S)-2-methylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-but-2-enoic acid methyl ester (55826-28-3,55870-59-2,64838-98-8,64838-99-9,79056-39-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Et₃N, ethyl chloroformate, 2.) Et₃N / 1.) ether, -25 deg C, 15 min, 2.) ether-CH₂Cl₂, 3 h, 0 deg C then 10-12 h at room temp.

2: water, p-toluenesulfonic acid monohydrate / acetone

3: 67 percent / triethylamine / CH₂Cl₂ / 0 °C

With water; chloroformic acid ethyl ester; toluene-4-sulfonic acid; triethylamine; In dichloromethane; acetone;

DOI:10.1016/S0040-4020(01)88885-2

upstream raw materials:

2-{(2R,3R)-2-[(2R,3R)-1-(1-Methoxycarbonyl-2-methyl-propenyl)-4-oxo-3-phenylacetylamino-azetidin-2-yldisulfanyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-3-methyl-but-2-enoic acid methyl ester

phosphorous acid trimethyl ester

1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanic acid methyl ester

2-[(2R)-2r-benzothiazol-2-yldisulfanyl-4-oxo-3c-(2-phenyl-acetylamino)-azetidin-1-yl]-3-methyl-but-2-enoic acid methyl ester

Downstream raw materials:

3-[(Phenylacetyl)amino]-2-azetidinone

1-(1'-methoxycarbonyl-2'-methylprop-1-enyl)-3-phenylacetamidoazetidin-2-one

methyl 2-<(3S)-3-benzyloxycarbonylamino-2-oxoazetidin-1-yl>-3-methylbut-2-enoate

(S)-3-[[(phenylmethyl)carbonyl]amino]-2-azetidinone

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