Cemandil sodium salt synthesis
- Product Name:Cemandil sodium salt
- CAS Number:42540-40-9
- Molecular formula:C19H17N6NaO6S2
- Molecular Weight:512.49
80543-51-7
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42540-40-9
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Yield:42540-40-9 96.3%
Reaction Conditions:
Stage #1:(6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid with N,O-bis-(trimethylsilyl)-acetamide in ethyl acetate at 25 - 28;
Stage #2:(S)-formyloxy(phenyl)acetyl chloride in ethyl acetate at 0 - 5; for 2 h;
Stage #3: with sodium hydrogencarbonate; pH=5.5 - 6.5Solvent;Temperature;
Steps:
1; 2 Example 1
Add 32.8g (0.1mol) of 7-ATCA and 200ml of ethyl acetate into a dry 500ml four-neck flask, control the temperature at 25-28 °C, add 40.8g (0.2mol) of BSA and stir the reaction for 4-6 h until it is clear; Cool down to 0-5 °C, add 23.8g (0.12mol) of L-formylmandelic acid chloride dropwise, stir and react for 2 h; After the 7-ATCA residue is less than 1.5mg/ml qualified, add 150ml of cold water at 0-10 °C. After stirring for 10 minutes, separate the layers, separate the water phase, and wash the organic phase with 100ml water and 100ml 20wt% sodium chloride solution in turn, then add 1.5g activated carbon and stir to decolorize for 1h;After filtering, washing with 50 ml of ethyl acetate, controlling the temperature of the organic phase within 45 °C and distilling to dryness under reduced pressure, 47.2 g of L-form cefmendol acid was obtained with a yield of 96.3%. Take 20g of L-form cefmendol acid and add 70g of 5% sodium bicarbonate solution dropwise,Control the PH value between 5.5 and 6.5, and use the BK-FD10S Brocade vacuum freeze dryer to freeze and dry at -45 to -40°C to obtain 20.5 g of product with a yield of 98%. Detection specific rotation: +36.5°.
References:
CN112694488, 2021, A Location in patent:Paragraph 0057-0064
![[6R-[6alpha,7beta(R*)]]-7-[(formyloxy)phenylacetamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid](/CAS/GIF/57268-80-1.gif)
57268-80-1
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42540-40-9
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42540-40-9
228 suppliers
$40.00/1 g
20698-91-3
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