(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(4-bromo-5,7-dioxo-2,2-diphenyl-5,7-dihydro-[1,3]dioxolo[4,5-f]isoindol-6-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

Chemical Name:(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(4-bromo-5,7-dioxo-2,2-diphenyl-5,7-dihydro-[1,3]dioxolo[4,5-f]isoindol-6-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS No.:153356-70-8
Molecular Formula:C₃₈H₂₉BrN₆O₁₁S₂
Molecular Weight:889.718
Hs Code.:

(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(4-bromo-5,7-dioxo-2,2-diphenyl-5,7-dihydro-[1,3]dioxolo[4,5-f]isoindol-6-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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Chemical Property of (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(4-bromo-5,7-dioxo-2,2-diphenyl-5,7-dihydro-[1,3]dioxolo[4,5-f]isoindol-6-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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Technology Process of (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(4-bromo-5,7-dioxo-2,2-diphenyl-5,7-dihydro-[1,3]dioxolo[4,5-f]isoindol-6-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 11 articles about (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(4-bromo-5,7-dioxo-2,2-diphenyl-5,7-dihydro-[1,3]dioxolo[4,5-f]isoindol-6-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 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: 61.0%

: 96628-33-0
3-(aminomethyl)-7-<2-(2-aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>ceph-3-em-4-carboxylic acid

: 153356-68-4
4-Bromo-5,7-dioxo-2,2-diphenyl-5,7-dihydro-[1,3]dioxolo[4,5-f]isoindole-6-carboxylic acid ethyl ester

: 153356-70-8
(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(4-bromo-5,7-dioxo-2,2-diphenyl-5,7-dihydro-[1,3]dioxolo[4,5-f]isoindol-6-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Guidance literature:: With triethylamine; In dimethyl sulfoxide; for 1.5h; Ambient temperature;
DOI:10.7164/antibiotics.46.1458

Reference yield:

: 68278-85-3
3-bromo-4,5-dimethoxy-toluene

: 153356-70-8
(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(4-bromo-5,7-dioxo-2,2-diphenyl-5,7-dihydro-[1,3]dioxolo[4,5-f]isoindol-6-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / SnCl₄ / 1,2-dichloro-ethane / 1.) 0 deg C, 20 min, 2.) RT, overnight

2: 25.6 percent / K₂CO₃, KMnO₄ / H₂O / 1 h / 90 - 95 °C

3: 100 percent / Ac₂O / 1 h / Heating

4: 100 percent / NH₄OH / Heating

5: 1.) BBr₃, 2.) H₂O / 1.) CH₂Cl₂, 2.) CH₂Cl₂, RT, 45 min

6: 62.5 percent / 3 h / 160 °C

7: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 3 h

8: 61 percent / Et₃N / dimethylsulfoxide / 1.5 h / Ambient temperature

With ammonium hydroxide; potassium permanganate; water; acetic anhydride; boron tribromide; tin(IV) chloride; sodium hydride; potassium carbonate; triethylamine; In water; dimethyl sulfoxide; 1,2-dichloro-ethane;
DOI:10.7164/antibiotics.46.1458

Reference yield:

: 2973-76-4
5-bromo-4-hydroxy-3-methoxybenzaldehyde

: 153356-70-8
(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(4-bromo-5,7-dioxo-2,2-diphenyl-5,7-dihydro-[1,3]dioxolo[4,5-f]isoindol-6-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 70 percent / K₂CO₃ / dimethylformamide / 72 h / Ambient temperature

2: 1.) hydrazine hydrate, 2.) KOH / 1.) diethylene glycol, 100 deg C, 4 5 min, 2.) diethylene glycol, 150 deg C, 3 h

3: 98 percent / SnCl₄ / 1,2-dichloro-ethane / 1.) 0 deg C, 20 min, 2.) RT, overnight

4: 25.6 percent / K₂CO₃, KMnO₄ / H₂O / 1 h / 90 - 95 °C

5: 100 percent / Ac₂O / 1 h / Heating

6: 100 percent / NH₄OH / Heating

7: 1.) BBr₃, 2.) H₂O / 1.) CH₂Cl₂, 2.) CH₂Cl₂, RT, 45 min

8: 62.5 percent / 3 h / 160 °C

9: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 3 h

10: 61 percent / Et₃N / dimethylsulfoxide / 1.5 h / Ambient temperature

With potassium hydroxide; ammonium hydroxide; potassium permanganate; water; acetic anhydride; boron tribromide; tin(IV) chloride; sodium hydride; potassium carbonate; hydrazine hydrate; triethylamine; In water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.7164/antibiotics.46.1458