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

HRID 2399844Notes

Reaction equation

COS(O)(=O)=O.B(OC)(OC)OC.CO.C[C:17]([O:19][CH2:20][C:21]1[CH2:30][S:29][C@@H:24]2[C@H:25]([NH2:28])[C:26](=[O:27])[N:23]2[C:22]=1[C:31]([OH:33])=[O:32])=O>CCCCCC.O1CCOCC1>[NH2:28][CH:25]1[C:26](=[O:27])[N:23]2[C:22]([C:31]([OH:33])=[O:32])=[C:21]([CH2:20][O:19][CH3:17])[CH2:30][S:29][C@H:24]12

Participants

Conditions

Temperature: -15 °C

Procedure

20.28 g of a methanolic solution of methoxysulfonic acid (prepared as described in Preparation 2), 2.20 g of trimethyl borate and 1.15 g of methanol were added to 3.5 ml of dioxane. The mixture was cooled to -15° C., and a suspended slurry of 2.74 g of 7-ACA in 15 ml of hexane were added thereto, followed by stirring at -6° C. for 5 hours. After completion of the reaction, the reaction mixture was treated following the procedures described in Example 2 to give 2.11 g (yield 86%) of the desired compound at a high purity.

Workup

customAfter completion of the reaction
additionthe reaction mixture was treated

Sources & evidence

ORD record: ord-76b2ab2af94a4f63bf7886483147ec41
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05451675

Reaction notes

Loading…