ampicillin (5-tert-butyl-2-oxo-1,3-dioxolen-4-yl)methyl ester hydrochloride

Base Information

• Chemical Name: ampicillin (5-tert-butyl-2-oxo-1,3-dioxolen-4-yl)methyl ester hydrochloride
• CAS No.: 93034-21-0
• Molecular Formula: C₂₄H₂₉N₃O₇S*ClH
• Molecular Weight: 540.037

Synonyms:ampicillin (5-tert-butyl-2-oxo-1,3-dioxolen-4-yl)methyl ester hydrochloride

Chemical Property of ampicillin (5-tert-butyl-2-oxo-1,3-dioxolen-4-yl)methyl ester hydrochloride

Chemical Property:

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Technology Process of ampicillin (5-tert-butyl-2-oxo-1,3-dioxolen-4-yl)methyl ester hydrochloride

There total 5 articles about ampicillin (5-tert-butyl-2-oxo-1,3-dioxolen-4-yl)methyl ester hydrochloride 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: 75.0%

(5-tert-butyl-2-oxo-1,3-dioxolen-4-yl)methyl 6β-aminopenicillanate p-toluenesulfonate (95477-81-9) + 2-(R)-2-phenyl-2-aminoacetyl chloride hydrochloride (40966-78-7,5321-31-3) → ampicillin (5-tert-butyl-2-oxo-1,3-dioxolen-4-yl)methyl ester hydrochloride (93034-21-0)

Guidance literature:

With ammonium bicarbonate; triethylamine; In dichloromethane; at 7 - 10 ℃; for 0.833333h;

DOI:10.1248/cpb.32.4316

Reference yield: 60.0%

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 5-tert-butyl-2-oxo-[1,3]dioxol-4-ylmethyl ester → ampicillin (5-tert-butyl-2-oxo-1,3-dioxolen-4-yl)methyl ester hydrochloride (93034-21-0)

Guidance literature:

With hydrogenchloride; In acetonitrile; at 0 - 5 ℃; for 0.5h; pH=2.0;

DOI:10.1248/cpb.32.2241

Reference yield:

2.2-Dimethyl-4-hydroxy-3-pentanone (52279-28-4) → ampicillin (5-tert-butyl-2-oxo-1,3-dioxolen-4-yl)methyl ester hydrochloride (93034-21-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) pyridine; 2.) p-toluenesulfonic acid / 1.) benzene, toluene, 0 deg C, overnight; 2.) reflux, 8 h

2: 66.4 percent / N-bromosuccinimide, α,α'-azobisisobutyronitrile / CCl4 / 1 h / Heating

3: 1.) potassium bicarbonate / 1.) DMF, 0 deg C, 3 h; 2.) 0 deg C, 3 h

4: 60 percent / 1N HCl / acetonitrile / 0.5 h / 0 - 5 °C / pH=2.0

With pyridine; hydrogenchloride; N-Bromosuccinimide; azobisisobutyronitrile; potassium hydrogencarbonate; toluene-4-sulfonic acid; In tetrachloromethane; acetonitrile;

DOI:10.1248/cpb.32.2241

upstream raw materials:

(5-tert-butyl-2-oxo-1,3-dioxolen-4-yl)methyl 6β-aminopenicillanate p-toluenesulfonate

2-(R)-2-phenyl-2-aminoacetyl chloride hydrochloride

2.2-Dimethyl-4-hydroxy-3-pentanone

4-tert-butyl-5-methyl-2-oxo-1,3-dioxolene

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