56187-47-4 Usage
Originator
Cefazedone Sodium,Arocor Holdings Inc.
Uses
Semi-synthetic cephalosporin antibiotic. Antibacterial.
Definition
ChEBI: A cephalosporin compound having [(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl and [(3,5-dichloro-4-oxopyridin-1(4H)-yl)acetamido side-groups.
Manufacturing Process
A solution of 1 eq. of the tert-butyl ester of 7-aminocephalosporanic acid and
1 eq. of dicyclohexylcarbodiimide in 100 ml of methylene chloride/DMF (1:1)
is cooled to 0°C. The mixture is combined with 1 eq. of 3,5-dichloro-4-
pyridone-1-acetic acid; after 5 min the ice bath is removed and the mixture
agitated for another 30 min at 25°C. The thus-formed urea is filtered off and
the filtrate filtered over silica gel (eluent: ethyl acetate/1% methanol). The
solvent is concentrated by evaporation, and the thus-obtained tert-butyl ester
of 7-(3,5-dichloro-1,4-dihydro-4-oxo-1-pyridylacetamido)cephalosporanic acid
is crystallized from ether.1 eq. of the tert-butyl ester is dissolved in 30 ml of trifluoroacetic acid. After
30 minutes, the solution is evaporated and the thus-produced 7-(3,5-dichloro-
1,4-dihydro-4-oxo-1-pyridylacetamido)cephalosporanic acid crystallized from
ether.1 eq. of the obtained 7-(3,5-dichloro-1,4-dihydro-4-oxo-1-pyridylacetamido)
cephalosporanic acid is dissolved in 60 ml of saturated aqueous sodium
bicarbonate solution at a pH of below 7 and combined with 1 eq. of 5-methyl-
1,3,4-thiadiazole-2-thiol in 20 ml of acetone. The reaction solution is agitated
for 2 hours at 80°C and at a pH of 6.3 under a nitrogen atmosphere. The
acetone is thereupon removed, the solution is washed with ether and acidified
to pH 2. The thus-obtained 3-(1-methyltetrazolyl-5-mercaptomethyl)-7-(3,5-
dichloro-1,4-dihydro-4-oxo-1-pyridylacetamido)-3-cephem-4-carboxylic acid is
filtered off and dried. IR spectrum confirmed the structure of cefazedone.In practice it is usually used as sodium salt.
Therapeutic Function
Antibiotic
Check Digit Verification of cas no
The CAS Registry Mumber 56187-47-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,6,1,8 and 7 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 56187-47:
(7*5)+(6*6)+(5*1)+(4*8)+(3*7)+(2*4)+(1*7)=144
144 % 10 = 4
So 56187-47-4 is a valid CAS Registry Number.
InChI:InChI=1/C18H19Cl2N5O5S3/c1-7-22-23-18(33-7)32-6-8-5-31-16-12(15(28)25(16)13(8)17(29)30)21-11(26)4-24-2-9(19)14(27)10(20)3-24/h9-10,12,16H,2-6H2,1H3,(H,21,26)(H,29,30)
56187-47-4Relevant articles and documents
Synthesis technology of cefazedone
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Paragraph 0043-0051, (2019/11/21)
The invention discloses a synthesis technology of cefazedone. A compound II reacts with 7-ACA to prepare a compound III, and the compound III reacts with a compound IV to prepare the product cefazedone (I). The technology has the advantages of simple synthesis route, mild reaction conditions, shortening of the reaction period, reduction of the production cost, increase of the total yield and the purity of the product, and suitableness for industrial production.
Preparation method of cefazedone
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Paragraph 0013; 0014; 0046; 0047; 0048; 0049; 0050-0054, (2017/08/29)
The invention discloses a preparation method of cefazedone. A starting material 7-amino acetoxyl-removed cepham acid (II) reacts with 3,5-dichloro pyridone acetate (III) to prepare a compound IV, the compound IV performs substitution reaction to obtain a compound V, the compound V reacts with 2-sulfydryl-5-methyl-1,3,4-thiadiazole to obtain a final product cefazedone. The cheap starting material reacts with a condensing agent, the reaction process is controllable, the operation is simple, the purity and the yield are high, and the method is suitable for industrial production.
