(pivaloyloxy)methyl 7α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-3-methylceph-3-em-4-carboxylate

Base Information

Chemical Name:(pivaloyloxy)methyl 7α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-3-methylceph-3-em-4-carboxylate
CAS No.:124093-85-2
Molecular Formula:C₂₄H₂₈N₂O₁₀S
Molecular Weight:536.56
Hs Code.:

Synonyms:(pivaloyloxy)methyl 7α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-3-methylceph-3-em-4-carboxylate

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Chemical Property of (pivaloyloxy)methyl 7α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-3-methylceph-3-em-4-carboxylate

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Technology Process of (pivaloyloxy)methyl 7α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-3-methylceph-3-em-4-carboxylate

There total 7 articles about (pivaloyloxy)methyl 7α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-3-methylceph-3-em-4-carboxylate 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: 23.0%

: 124093-84-1
(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-1-oxopenicillanate

: 124093-85-2
(pivaloyloxy)methyl 7α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-3-methylceph-3-em-4-carboxylate

Guidance literature:: With pyridine; phosphoric acid; In 1,4-dioxane; for 20h; Heating;
DOI:10.1021/jm00163a048

Reference yield:

: 18997-19-8
Chloromethyl pivalate

: 124093-85-2
(pivaloyloxy)methyl 7α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-3-methylceph-3-em-4-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 12.6 percent / Et₃N, KHCO₃ / dimethylformamide / 21 h / Ambient temperature

2: 1.) tert-BuMgCl, 2.) / 1.) THF, ether, -78 deg C, 1 h, 2.) -78 deg C, 1 h

3: 70 percent / H₂ / 10percent Pd/C / H₂O; tetrahydrofuran / 1.5 h

4: 97 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Ambient temperature

5: 50 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / 0 °C

6: 23 percent / 80percent phosphoric acid, pyridine / dioxane / 20 h / Heating

With pyridine; dmap; phosphoric acid; tert-butylmagnesium chloride; hydrogen; potassium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00163a048

Reference yield:

: 69388-93-8
6,6-dibromopenicillanic acid pivaloyloxymethyl ester

: 124093-85-2
(pivaloyloxy)methyl 7α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-3-methylceph-3-em-4-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) tert-BuMgCl, 2.) / 1.) THF, ether, -78 deg C, 1 h, 2.) -78 deg C, 1 h

2: 70 percent / H₂ / 10percent Pd/C / H₂O; tetrahydrofuran / 1.5 h

3: 97 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Ambient temperature

4: 50 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / 0 °C

5: 23 percent / 80percent phosphoric acid, pyridine / dioxane / 20 h / Heating

With pyridine; dmap; phosphoric acid; tert-butylmagnesium chloride; hydrogen; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;
DOI:10.1021/jm00163a048