Ammonia → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

HRID 1167980Notes

Reaction equation

C[C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.CS(O)(=O)=O.B(OC)(OC)OC.N>C(Cl)Cl>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][O:4][CH3:2])[CH2:15][S:14][C@H:9]12

Participants

Conditions

Temperature: 0 °C

Procedure

10 g of 7-aminocephalosporanic acid was added to 80 ml of methylene chloride and the resulting mixture was cooled to 0° C., and then, 36.2 m of methanesulfonic acid was added slowly thereto. 7.4 ml of trimethyl borate was added thereto at the above temperature and the resulting mixture was stirred at 0 ° C. for 5 hours, and then, the resulting mixture was added to ice-water. The pH of the mixture was adjusted to 3.5 with aqueous ammonia. The ocherous solid formed was isolated by filtration and washed with water. The wet solid was dispersed in water and adjusted the pH to 8 with aqueous ammonia to dissolve the solid in water. Thereafter, the pH of the resulting mixture was adjusted to 3.5 with 3N hydrochloric acid. The resulting mixture was filtered to obtain crystals and the crystals were washed with water and then, dried overnight in a vacuum to give 2.32 g of 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid as an ocherous solid (Yield: 26% and Purity: 95.5%). H-NMR data was equal to that of the compound prepared in Example 1.

Workup

customThe ocherous solid formed
customwas isolated by filtration
washwashed with water
additionThe wet solid was dispersed in water
dissolutionto dissolve the solid in water
filtrationThe resulting mixture was filtered
customto obtain crystals
washthe crystals were washed with water
customdried overnight in a vacuum

Sources & evidence

ORD record: ord-c8abbdbea689452cb0bcebf53af22b5d
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06620930B1

Reaction notes

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