6-APA

6-Aminopenicillanic acid

IUPAC name (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4- thia-1-azabicyclo[3.2.0]heptane-2- carboxylic acid
Identifiers
CAS number	551-16-6^Y
PubChem	11082
ChemSpider	10611^Y
ChEBI	CHEBI:57869^Y
Jmol-3D images	Image 1
SMILES O=C(O)[C@@H]1N2C(=O)[C@@H](N)[C@H]2SC1(C)C
InChI InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1^Y Key: NGHVIOIJCVXTGV-ALEPSDHESA-N^Y InChI=1/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1 Key: NGHVIOIJCVXTGV-ALEPSDHEBW
Properties
Molecular formula	C₈H₁₂N₂O₃S
Molar mass	216.25 g/mol
Melting point	198 - 200 °C
Boiling point	> 200 °C (decomposes)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

6-APA is the chemical compound (+)-6-aminopenicillanic acid. ^[1]

1 Use
2 Manufacture
3 References
4 External links
5 See also

Use

6-APA is the core of penicillins. It is obtained from the fermentation brew of the Penicillium mold and used as the main starting block for the preparation of numerous semisynthetic penicillins.

Manufacture

This useful compound is made as follows:

Weissenburger, H. W. O.; Van der Hoven, M. G.; Recl. Trav. Chim. Pays-Bas 1970, 89, 1081.

References

^ F.P. Doyle, J.H.C. Nayler, G.N. Rolinson US Patent 2,941,995, filed July 22, 1958, granted June 21, 1960. Recovery of solid 6-aminopenicillanic acid.

External links

US 2,941,995 on espacenet

6-APA

Contents

Use

Manufacture

References

External links

See also