7-Amino-3 chloromethyl-3-cephem-4-carboxylic Acid p-Methoxybenzyl Ester Hydrochloride Chemical Properties

Melting point:

155-157°C

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

Pale Yellow to Pale Beige

Stability:

Hygroscopic

InChI

InChI=1/C16H17ClN2O4S.ClH/c1-22-11-4-2-9(3-5-11)7-23-16(21)13-10(6-17)8-24-15-12(18)14(20)19(13)15;/h2-5,12,15H,6-8,18H2,1H3;1H/t12-,15-;/s3

InChIKey

LYIIGHOYDRRHAJ-JQWYMVCGNA-N

SMILES

C(C1=C(CS[C@]2([H])[C@H](N)C(=O)N12)CCl)(=O)OCC1C=CC(OC)=CC=1.Cl |&1:5,7,r|

7-Amino-3 chloromethyl-3-cephem-4-carboxylic Acid p-Methoxybenzyl Ester Hydrochloride Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

Cefazolin intermediate as antibacterials.

Uses

7-Amino-3 chloromethyl-3-cephem-4-carboxylic Acid p-Methoxybenzyl Ester Hydrochloride can be used as a pharmaceutical intermediate for Cefiderocol, a novel iron-carrying cephalosporin antibiotic for the treatment of complicated urinary tract infections.

Synthesis

Synthesis of (6R,7R)-4-methoxybenzyl (6R,7R)-4-methoxybenzyl 7-amino-3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thiophene-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate as (6R,7R)-4-methoxybenzyl 7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2 -ene-2-carboxylate hydrochloride was carried out in the following general procedure: dichloromethane (3 L) and phosphorus pentachloride (374.4 g) were added to a 10 L reaction flask, and the reaction system was cooled to about 0 °C. Pyridine (200mL) was slowly added dropwise, with the rate of dropwise acceleration controlled to maintain an internal temperature of no more than 5°C. After 1 hour of reaction, the system was further cooled to -5 °C and GCLE (7-phenylacetamido-3-chloromethylbenzyl methoxyacrylate p-methoxybenzyl ester of cerebral alanine acrylate, 584.4 g) was added in batches, keeping the internal temperature between -5 and 0 °C, and the reaction was continued for 3 hours. The reaction was rapidly cooled to -30 °C, methanol (1500 mL) was slowly added dropwise and kept at -30 °C for 1 hour. The temperature was then raised to -10°C, water (1500mL) was added dropwise, and the reaction was controlled at a temperature between -10 and 0°C for 1 hour. Finally, water (1500 mL) was added and stirred for 5 minutes. The reaction mixture was poured into a beaker with a lower spout and left to stratify. The organic phase was separated and the aqueous phase was extracted with a small amount of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate (1000 g), filtered, and the filter cake was washed with a small amount of dichloromethane. The filtrate was slowly added dropwise to isopropyl ether (12 L) and stirred overnight. On the next day, the solid was collected by filtration and washed with a small amount of isopropyl ether to give a pale yellow solid. The solid was scraped off and dried under vacuum overnight to give a final product of 456g.

References

[1] Patent: CN106317077, 2017, A. Location in patent: Paragraph 0010; 0011l 0012

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