Pyridine → HCID 123160304, compound

HRID 655053

Reaction equation

HRID 655053 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:29])[C@@H:18]([NH:19]C(=O)CC4C=CC=CC=4)[C@H:15]3[S:14][CH2:13][C:12]=2[CH2:30][Cl:31])=[O:10])=[CH:5][CH:4]=1.CN1CCOCC1.N1C=CC=CC=1.[C:47]([O:51][C:52]([NH:54][C:55]1[S:56][CH:57]=[C:58]([C:60](=[N:64][O:65][CH3:66])[C:61](Cl)=[O:62])[N:59]=1)=[O:53])([CH3:50])([CH3:49])[CH3:48]>ClCCl.O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:29])[C@@H:18]([NH:19][C:61](=[O:62])[C:60]([C:58]4[N:59]=[C:55]([NH:54][C:52]([O:51][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:53])[S:56][CH:57]=4)=[N:64][O:65][CH3:66])[C@H:15]3[S:14][CH2:13][C:12]=2[CH2:30][Cl:31])=[O:10])=[CH:32][CH:33]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 79724-MethylmorpholineHCID 10874591(4-Methoxyphenyl)methyl (6R,7R)-3-(chloromethyl)-8-oxo-7-((2-phenylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylateHCID 53903221HCID 53903221, compound

Product 1

HCID 123160304HCID 123160304, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of 7β-amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (1) p-toluenesulfonate (4.33 g; 8 mMol.) in dichloromethane (40 ml) is added at 0° C. N-methylmorpholine (0.88 g; 1 Eq.), pyridine (0.8 ml; 1.2 Eq.) and 2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-methoxyiminoacetyl chloride (1.2 Eq.). After keeping at 0° C. for 30 minutes, the reaction mixture is diluted with water and ethyl acetate and ethyl acetate layer is taken. This is washed with ##STR19## water, dried and concentrated under reduced pressure. The residue is purified by silica gel chromatography (using toluene:ethyl acetate) to give 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (2) (4.89 g).

Workup

  1. additionis added at 0° C
  2. washThis is washed with ##STR19## water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel chromatography (using toluene:ethyl acetate)

Sources & evidence

ORD record
ord-2e70054aa9af4718b8da2635ea424b74
Source dataset
uspto-grants-1992_07
Patent number
US05134138

Linked notes

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