ChemicalBook CAS DataBase List Flomoxef Impurity 5

Flomoxef Impurity 5 synthesis

8synthesis methods

Product Name:Flomoxef Impurity 5
CAS Number:134237-56-2
Molecular formula:C25H23ClF2N2O6S
Molecular Weight:552.97

451 mL ofdichloromethane, 2- (difluoro-methylthio) acetic acid 49.6 g, 144.8 mL pyridine was added to reactorand cooled to -40 ° C. (6R, 7R)-benzhydryl-7-amino-3-(chloromethyl)-7-methoxy-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylatein dichloromethane 1080 mL was added to the reactor and temperature wasmaintained at -25 ° C. After the reactionsolution was cooled below -45 ° C, 42 mL of phosphorous oxychloride in 180.4 mLdichloromethane was added at -15°C and stirred for 30 minutes. After checking completion of the reaction1262.8 ml of purified water, 4.59 ml of 35% hydrochloric acid, 2.7 ml of 50%tetrabutylammonium bromide was added dropwise at 0°C, which in turn stirred for10 minutes. Then, 1262.8 ml of methanol was added at 0°C and stirred for 10 minutes. then separating the layer. 902 mL ethanol added to the filtrate and then stirred for 2 hours at -10 and washed with 360.8 mL of ethanol, and a white or slightly yellow horse crystal component of the vacuum-dried for 10 hours at 40 was added (6R,7R)-benzhydryl (7-(2-difluoromethylthio)acetamido)-3-(chloromethyl)-7-methoxy-8-oxo-5-oxa-1-aza-bicyclo[4,2,0]oct-2-ene-2-carboxylate (146.7g, 76%).

5-Oxa-1-azabicyclo 4.2.0 oct-2-ene-2-carboxylic acid, 3-(chloroMethyl)-7- (4-Met

91177-27-4
37 suppliers
inquiry

134237-56-2
18 suppliers
inquiry

Yield:-

Steps:

Multi-step reaction with 3 steps
1: tert-butylhypochlorite / methanol; dichloromethane / -45 °C
2: pyridine; phosphorus pentachloride / methanol; dichloromethane / -40 °C
3: pyridine; trichlorophosphate / methanol; dichloromethane / -40 - 0 °C

References:

He, Yi;Wu, Jian Bo;Lei, Fan;Chen, Pei;Hai, Li;Wu, Yong [Chinese Chemical Letters,2012,vol. 23,# 4,p. 407 - 410]

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-6-[(4-methylbenzoyl)amino]-7-oxo-, (2S,5R,6R)-

17028-66-9
0 suppliers
inquiry

134237-56-2
18 suppliers
inquiry

References

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-6-[(4-methylbenzoyl)amino]-7-oxo-, diphenylmethyl ester, 4-oxide, [2S-(2α,5α,6α)]-

82468-41-5
0 suppliers
inquiry

134237-56-2
18 suppliers
inquiry

References

4-Oxa-2,6-diazabicyclo[3.2.0]hept-2-ene-6-acetic acid, α-(1-Methylethenyl)-3-(4-Methylphenyl)-7-oxo-, diphenylMethyl ester, [1R-[1α,5α,6(R*)]]- (9CI)

67978-05-6
35 suppliers
inquiry

134237-56-2
18 suppliers
inquiry

References

68313-81-5 Synthesis

(2R,6R,7R)-3-Methylene-7-(p-toluoylamino)-8-oxo-5-oxa-1-azabicyclo[4.2.0]octane-2-carboxylic acid diphenylmethyl ester

68313-81-5
18 suppliers
$502.04/5MG

134237-56-2
18 suppliers
inquiry

References