Monomethyl sulfate → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid
Reaction equation
COS(O)(=O)=O.B(OC)(OC)OC.C[C:15]([O:17][CH2:18][C:19]1[CH2:28][S:27][C@@H:22]2[C@H:23]([NH2:26])[C:24](=[O:25])[N:21]2[C:20]=1[C:29]([OH:31])=[O:30])=O>C(OC)(=O)CCCCC(OC)=O>[NH2:26][CH:23]1[C:24](=[O:25])[N:21]2[C:20]([C:29]([OH:31])=[O:30])=[C:19]([CH2:18][O:17][CH3:15])[CH2:28][S:27][C@H:22]12Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
17.9 g of a methanolic solution of methoxysulfonic acid (prepared as described in Preparation 4) and 1.04 g of trimethyl borate were added to 20 ml of dimethyl adipate. The mixture was cooled to 15° C. and 2.74 g of 7-ACA were added thereto, followed by stirring at 15° C. for 1.5 hours. After completion of the reaction, the reaction mixture was treated following the procedures described in Example 2 to give 2.06 g (yield 84%) of the desired compound with a high purity.
Workup
- customAfter completion of the reaction
- additionthe reaction mixture was treated
Sources & evidence
- ORD record
- ord-1dde67d2bbf74201a1cd8c080c8a2bad
- Source dataset
- uspto-grants-1995_09
- Patent number
- US05451675
Reaction notes
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