(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate
- CAS No.
- 173604-87-0
- Chemical Name:
- (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate
- Synonyms
- (5-Methyl-2-oxo-1,3-dioxol-4-yl)methylp-nitrophenyl carbonate;(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate;Carbonic acid, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl -ester;carbonic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester 4-nitro-phenyl ester
- CBNumber:
- CB01876499
- Molecular Formula:
- C12H9NO8
- Molecular Weight:
- 295.2
- MDL Number:
- MFCD04035556
- MOL File:
- 173604-87-0.mol
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS03,GHS09 |
|---|---|
| Signal word | Warning |
| Hazard statements | H272-H411 |
| Precautionary statements | P210-P220-P221P280-P370+P378-P501 |
(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate Chemical Properties,Uses,Production
Uses
(5-Methyl-2-oxo-1,3-dioxol-4-YL)methyl 4-nitrophenyl carbonate is a pharmaceutical intermediate compound for the preparation of Ceftobiprole medocaril, a broad-spectrum, 5th generation cephalosporin with activity against gram-positive bacteria (e.g. methicillin-resistant).
Synthesis
(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate is prepared by the reaction of 4-Nitrophenyl chloroformate and Bis(4-nitrophenyl) carbonate. The specific synthesis steps are as follows:
4-Hydroxymethyl-5-methyl-1,3-doxolene-2-one (5.59 g) and pyridine (3.74 g) were dissolved in 50 mL of chloroform and cooled in an ice bath. 4-Nitrophenylchloroformate (9.46 g) dissolvedin chloroform (50 mL) was added dropwise to the above solution.
The mixture was stirred for 16 hours at room temperature.
The reaction mixture was cooled in ice and washed with ice cold 1percent sodium hydroxide, 1N hydrochloric acid, water and brine and dried over sodium sulfate.
Evaporation of the organic layer resulted in 11.2 g of crude product, which was crystallized from chloroform/hexane.
The crystals formed were filtered and washed with ice cold hexane/chloroform (1:1), to obtain the pure 4-nitrophenyl carbonate (9.11 g, 81percent); mp 116°-117°; 1 H NMR (CDCl3) δ2.23 (s, 3H), 5.05 (s,2H), 7.41 (d, 2H), 8.3 (s, 2H); 13 C NMR (CDCl3), δ9.43, 58.07, 121.69, 121.35, 132.15, 141.42, 145.57, 151.66, 152.19, 155.05; IR (KBr) 1779, 1811, 1525, 1247, 1221, 1207 cm-1.
(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate Preparation Products And Raw materials
Raw materials
Preparation Products
(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
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