7-AVCA Chemical Properties

Melting point:

215-220°C

Boiling point:

540.7±50.0 °C(Predicted)

Density 

1.55±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

Aqueous Base (Slightly), DMSO (Slightly)

form 

Solid

pka

2.73±0.50(Predicted)

color 

White to Pale Yellow

InChI

InChI=1S/C9H10N2O3S/c1-2-4-3-15-8-5(10)7(12)11(8)6(4)9(13)14/h2,5,8H,1,3,10H2,(H,13,14)/t5-,8-/m1/s1

InChIKey

GQLGFBRMCCVQLU-SVGQVSJJSA-N

SMILES

N12[C@@]([H])([C@H](N)C1=O)SCC(C=C)=C2C(O)=O

CAS DataBase Reference

79349-82-9(CAS DataBase Reference)

7-AVCA Usage And Synthesis

Chemical Properties

White Solid

Uses

A key intermediate in the manufacturing of Cephalosporin compounds.

Synthesis

The general procedure for the synthesis of (6R,7R)-7-amino-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid from cefixime impurity is as follows: 25.5 g (0.05 mol) of GVNA was placed in a 1,000 mL three-necked flask fitted with a thermometer and a mechanical stirrer, and 300 g of phenol and 2.8 g of acetic acid and the reaction was held at 35°C. After the reaction was complete (about 6 hours), the reaction mixture was slowly poured into a mixed solution consisting of sodium bicarbonate, purified water, and butyl acetate (5 g of purified water, 200 mL of purified water, and 200 mL of butyl acetate). The aqueous phase was extracted twice with 50 mL of butyl acetate and the aqueous phases were combined. The aqueous phase was transferred to a 500 mL reaction flask and stirred at room temperature for 2 hours. 4 g of immobilized acyltransferase PGA-450 was added, followed by dropwise addition of 15% aqueous sodium carbonate solution, maintaining the pH between 8.0-8.2 until the HPLC assay showed less than 0.5% GVNA. The enzyme was recovered by filtration. The filtrate was collected and the pH was adjusted with 10% hydrochloric acid to 3.4. The filter cake was washed with 50 mL of acetone and dried to give 10.7 g of AVNA (93.8% yield as GVNA).

References

[1] Patent: CN104045655, 2016, B. Location in patent: Paragraph 0061
[2] Organic Process Research and Development, 2009, vol. 13, # 5, p. 924 - 927
[3] Patent: CN103923104, 2016, B. Location in patent: Paragraph 0032-0034

7-AVCA(79349-82-9)Related Product Information

• N-Vinyl-2-pyrrolidone
• Triethoxyvinylsilane
• 4-(4-CHLORO-BENZYLOXY)-PHENYLAMINE
• VINYL PROPIONATE
• (6R-trans)-7-[[(2-AMino-4-thiazolyl)acetyl]aMino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
• (6R,7R)-7-((Z)-2-(2-aMinothiazol-4-yl)-2-(hydroxyiMino)acetaMido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 5-oxide
• (Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamide
• (Z)-Cefdinir
• Cefdinir Impurity E
• H-D-PHG-OME HCL
• 3-Hydroxy-4-Methyl-2(5H)-thiophenone
• Cefdinir Impurity M
• Phenylglycylcefalexin
• (6R,7R)-7-(4-Hydroxyisoxazole-3-carboxaMido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
• 2-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acid
• D(-)-Phenylglycinamide
• Cefdinir Impurity N
• (6R-trans)-7-[(2,2-diMethyl-1-oxopropyl)aMino]-3-Methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-