(pivaloyloxy)methyl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate

Base Information

Chemical Name:(pivaloyloxy)methyl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate
CAS No.:80903-77-1
Molecular Formula:C₂₄H₃₀N₂O₉
Molecular Weight:490.51
Hs Code.:

Synonyms:(pivaloyloxy)methyl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate

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Chemical Property of (pivaloyloxy)methyl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate

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Technology Process of (pivaloyloxy)methyl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate

There total 7 articles about (pivaloyloxy)methyl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-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: 7.0%

: 80903-76-0
(pivaloyloxy)methyl 1-hydroxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate

: 108-24-7
acetic anhydride

: 80903-77-1
(pivaloyloxy)methyl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate

Guidance literature:: With pyridine; dmap; In dichloromethane; at -10 ℃; for 1h;
DOI:10.1021/jm00163a048

Reference yield:

: 10209-11-7
(6R,7R)-3-Methyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

: 80903-77-1
(pivaloyloxy)methyl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / Et₃N, KHCO₃ / dimethylformamide / 24 h

2: 54 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 0 - 5 °C

3: 48 percent / diisopropylethylamine, potassium tert-butoxide, picryl azide / CH₂Cl₂ / 0.5 h / 0 °C

4: CH₂Cl₂ / 0.5 h / -55 °C / Irradiation

5: Rieke zinc powder, acetic acid / tetrahydrofuran / 1 h / 0 - 5 °C

6: 13 percent / tetrabutylammonium borohydride / CH₂Cl₂ / 1 h / -78 °C

7: 7 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / -10 °C

With pyridine; dmap; 2-azido-1,3,5-trinitro-benzene; potassium tert-butylate; tetrabutylammonium borohydride; potassium hydrogencarbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00163a048

Reference yield:

: 18997-19-8
Chloromethyl pivalate

: 80903-77-1
(pivaloyloxy)methyl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / Et₃N, KHCO₃ / dimethylformamide / 24 h

2: 54 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 0 - 5 °C

3: 48 percent / diisopropylethylamine, potassium tert-butoxide, picryl azide / CH₂Cl₂ / 0.5 h / 0 °C

4: CH₂Cl₂ / 0.5 h / -55 °C / Irradiation

5: Rieke zinc powder, acetic acid / tetrahydrofuran / 1 h / 0 - 5 °C

6: 13 percent / tetrabutylammonium borohydride / CH₂Cl₂ / 1 h / -78 °C

7: 7 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / -10 °C

With pyridine; dmap; 2-azido-1,3,5-trinitro-benzene; potassium tert-butylate; tetrabutylammonium borohydride; potassium hydrogencarbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00163a048