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86273-18-9

Basic Information
CAS No.: 86273-18-9
Name: LENAMPICILLIN
Molecular Structure:
Molecular Structure of 86273-18-9 (LENAMPICILLIN)
Formula: C21H23 N3 O7 S
Molecular Weight: 461.49
Synonyms: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-,(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester, [2S-[2a,5a,6b(S*)]]-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-,(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester, (2S,5R,6R)- (9CI); 1,3-Dioxole,4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid deriv.; Antibiotic KBT1585; Lenampicillin
Density: 1.47g/cm3
Hazard Symbols: Xi
Risk Codes: 36/37/38
PSA: 170.38000
LogP: 1.86060
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Chemistry

IUPAC Name: (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,
3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Molecular Formula: C21H23N3O7
Freely Rotating Bonds: 8
Polar Surface Area: 130.99 Å2
Index of Refraction: 1.653
Molar Refractivity: 114.31 cm3
Molar Volume: 311.9 cm3
Polarizability: 45.31 ×10-24cm3
Surface Tension: 70.1 dyne/cm 
Density: 1.47 g/cm3
The Cas Register Number of Lenampicillin  is 86273-18-9 .The chemical synonyms of Lenampicillin (CAS No. 86273-18-9) are Lenampicillin ; Lenampicillin hydrochloride ; 1,3-Dioxole, 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid deriv. ; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester, [2s-[2a,5a,6b(s*)]]- ; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2r)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester, (2s,5r,6r)- (9ci) ; Antibiotic kbt 1585 ; Lenanpicillin ; Varacllin .The molecular structure of Lenampicillin (CAS No. 86273-18-9) is.

Uses

It is widely used as Acute bronchitis, pneumonia, pulmonary suppuration syndrome, pharyngitis, trauma and surgical wound such as a table of secondary infection, periodontal tissue inflammation, otitis media and so on.

Production

To 6-APA as raw material, to maintain amino methyl acetoacetate, l0g 6-APA suspended in 100ml dichloromethane and l0ml methanol, at room temperature by adding 9ml triethylamine and 6.5g methyl acetoacetate, and then stirred at room temperature 2h. Decompression was concentrated, residue of compound (I), used directly for next step reaction.
The compound (I) dissolved in 70ml ethyl acetate and 18ml N, N-dimethyl formamide, at 50 ℃ by adding 1.7g of potassium bicarbonate, 1.2g of sodium iodide, and 8.2g 4 - chloro-methyl-5-A-1,3-dioxo-cyclopentene-2- one, at room temperature, stirring 15h. Add 40ml cold water, intense mixing 10min. Separation of the organic layer with 5% sodium chloride solution (2 × 40m1) Wash, dry and anhydrous magnesium sulfate. Drying off the organic layer containing compound (Ⅱ), without purification, used directly for next step reaction.
The above obtained compound (Ⅱ) solution cooling to 0 ~ 5 ℃, the stirring by adding 8.7g p-toluenesulfonic acid hydrate in 25ml ethyl acetate in a single solution. Within a few minutes that the precipitates crystalline precipitation, the suspension of 5 ~ 1012 to continue stirring 30min e, filter to collect precipitation precipitation, washing with ethyl acetate, may 20.4g compounds (Ⅲ), melting point 157 ~ 160 ℃ (decomposition ). Three-step total yield of 88%.
10g compounds (Ⅲ) suspended in 100ml dichloromethane solution, in 0 ~ 5 ℃ and stirring, add 2.8ml triethylamine and 4g ammonium bicarbonate. In a phased manner over 15min by adding 5g of benzene Gly-chloride, and then in the 7 ~ 10 ℃ under stirring 50min. Add 70ml water, under the 0 ~ 5 ℃ with 3mol / L sodium hydroxide solution transferred Ph7.4. After filtration, separation of methylene chloride layer washed with 5% sodium chloride solution. In the 0 ~ 5 ℃ and stirring, to the dichloromethane solution by adding 80ml saturated saline, then add 2mol / L hydrochloric acid to the Ph value of 1.5. Separation of the organic layer, washed with saturated brine, anhydrous magnesium sulfate drying. Decompression was concentrated, residue crystals with 40ml 2-butanone .
Coarse crystals soluble in dichloromethane, vacuum concentration was a residue, add 20ml isopropyl alcohol and 40ml ethyl acetate, in place overnight under 5 ℃. Obtained colorless crystals filtered, washed with cold ethyl acetate, may 7.6g lenampicillin hydrochloride, yield 76%, melting point 145 ℃ (decomposition).
Method 2: ampicillin as raw material. Ampicillin and dehydration condensation of benzaldehyde to form a Schiff's base while ampicillin on the protection of free amino, and then, and 4 - halogen-methyl -5 - methyl-1,3 - dioxa -4 - cyclopentene -2 - one (halogen = bromine or chlorine) reaction, the introduction of two on the chain, and finally methanol solution of hydrogen chloride acid decomposition Schiff's base, off to protect the base and get lenampicillin the hydrochloride.

Toxicity Data With Reference

1.    

orl-rat LD50:10 g/kg

    NKRZAZ    Chemotherapy (Tokyo). 32 (Suppl 8)(1984),31.
2.    

scu-rat LD50:4362 mg/kg

    NKRZAZ    Chemotherapy (Tokyo). 32 (Suppl 8)(1984),31.
3.    

ivn-rat LD50:838 mg/kg

    NKRZAZ    Chemotherapy (Tokyo). 32 (Suppl 8)(1984),31.
4.    

orl-mus LD50:8294 mg/kg

    NKRZAZ    Chemotherapy (Tokyo). 32 (Suppl 8)(1984),31.
5.    

scu-mus LD50:3576 mg/kg

    NKRZAZ    Chemotherapy (Tokyo). 32 (Suppl 8)(1984),31.
6.    

ivn-mus LD50:711 mg/kg

    NKRZAZ    Chemotherapy (Tokyo). 32 (Suppl 8)(1984),31.

Safety Profile

Moderately toxic by intravenous and subcutaneous routes. Mildly toxic by ingestion. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx, NOx, and HCl. See also ESTERS.
Hazard Codes: IrritantXi  
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.