methyl (2R,3R)-2-(2'-benzothiazolylthio)-α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate

Base Information

• Chemical Name: methyl (2R,3R)-2-(2'-benzothiazolylthio)-α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate
• CAS No.: 64370-26-9
• Molecular Formula: C₂₄H₂₃N₃O₅S₃
• Molecular Weight: 529.662
• Mol file: 64370-26-9.mol

Synonyms:methyl (2R,3R)-2-(2'-benzothiazolylthio)-α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate

Chemical Property of methyl (2R,3R)-2-(2'-benzothiazolylthio)-α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3R)-2-(2'-benzothiazolylthio)-α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate

There total 5 articles about methyl (2R,3R)-2-(2'-benzothiazolylthio)-α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate 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: 98.0%

methyl (2R,3R)-2-(benzothiazol-2'-yldithio)-α-isopropenyl-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate (40578-84-5,57031-02-4) → methyl (2R,3R)-2-(2'-benzothiazolylthio)-α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate (64370-26-9)

Guidance literature:

With pyridine; for 48h;

Reference yield: 53.0%

methyl (2R,3R)-2-(benzothiazol-2'-yldithio)-α-isopropenyl-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate (40578-84-5,57031-02-4) → methyl (2R,3R)-2-(2'-benzothiazolylthio)-α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate (64370-26-9) + 3-Methyl-2-[3-oxo-4-(2-phenoxy-acetylamino)-3H-isothiazol-2-yl]-but-2-enoic acid methyl ester (22297-57-0) + 2-[(1R,2R)-1-(Benzothiazol-2-yldisulfanyl)-2-carboxy-2-(2-phenoxy-acetylamino)-ethylamino]-3-methyl-but-2-enoic acid methyl ester (115203-90-2) + dimethyl 2,2'-dithiobis(α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate) (75261-30-2,87678-52-2)

Guidance literature:

With triethylamine; In dichloromethane; at 15 - 20 ℃; for 1.5h;

Reference yield:

phenoxymethylpenicillin sulfoxide (4888-90-8) → methyl (2R,3R)-2-(2'-benzothiazolylthio)-α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate (64370-26-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Et₃N, N-methylmorpholine, methyl chloroformate / 1.) acetone,water, -20 deg C to -15 deg C, 20 min, 2.) acetone, water, 5 deg C - 10 deg C, 2 h

2: 90 percent / butyl acetate / 3.5 h / Heating

3: 98 percent / pyridine / 48 h

With 4-methyl-morpholine; pyridine; triethylamine; methyl chloroformate; In acetic acid butyl ester;

upstream raw materials:

methyl (2R,3R)-2-(benzothiazol-2'-yldithio)-α-isopropenyl-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate

phenoxymethylpenicillin sulfoxide

methyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide

Downstream raw materials:

(3R,4R)-4-(benzothiazol-2-yl)dithio-3-phenoxyacetamido-2-oxoazetidine

dimethyl 2,2'-dithiobis(α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate)

2-phenoxymethyl-4-(2'-methylprop-1'-enylaminocarbonyl-1'-methyloxycarbonyl)thiazole

2-Mercaptobenzothiazole