3-(2-Bromo-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one

Chemical Properties

yellow powder.

Uses

3-(2-Bromo-1-oxopropyl)-spiro[2h-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one is an intermediate of meropenem, and meropenem is a carbapenem antibiotic, which is suitable for the treatment of meningitis.

Application

A useful research chemical compound.

Synthesis

Comparative Example 1: 1.4,80 g of spiro[benzo[e][1,3]oxazine-2,1'-cyclohexyl]-4(3H)-one, 127 g of 2-bromopropionyl bromide, and 40 g of pyridine (molar ratio 1:1.6:1) were dissolved in chlorobenzene (mass ratio 1:4.4). The mixture was placed in a four-necked flask under nitrogen protection and reacted at 50 °C for 8 hours. After completion of the reaction, the mixture was washed three times with 200 g of water, three times with 200 g of 10% potassium hydroxide solution and three times with 200 g of water, in that order. The organic phases were combined and concentrated under reduced pressure to remove the solvent to obtain a colorless liquid. To this liquid was added 80 g of ethanol (mass ratio 1:1), cooled to -5 °C, stirred for 2 h, filtered and dried to give 109 g of 3-(2-bromo-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1 '-cyclohexyl]-4(3H)-one. The molar yield was 84.5% and the purity was 97.9%.

storage

Store the container tightly closed in a dry, cool and well-ventilated place. Store apart from foodstuff containers or incompatible materials.

References

[1] Journal of Organic Chemistry, 1995, vol. 60, # 5, p. 1096 - 1097
[2] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 23, p. 2851 - 2856
[3] Journal of Organic Chemistry, 1997, vol. 62, # 9, p. 2877 - 2884
[4] Patent: CN106432122, 2017, A. Location in patent: Paragraph 0070-0072
[5] Patent: US5442055, 1995, A