Water → HCID 131712824, compound

HRID 2296577Notes

Reaction equation

[CH3:1][C:2]1[CH2:11][S:10][C@@H:5]2[C@H:6]([NH2:9])[C:7](=[O:8])[N:4]2[C:3]=1[C:12]([OH:14])=[O:13].O.[C:16](=O)(O)[O-].[Na+].C[C:22]1[O:26][N:25]=[C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:23]=1[C:33](Cl)=[O:34]>CC(C)=O>[CH3:1][C:2]1[CH2:11][S:10][C@@H:5]2[CH:6]([NH:9][C:33]([C:23]3[C:24]([C:27]4[CH:28]=[C:29]([CH3:16])[CH:30]=[CH:31][CH:32]=4)=[N:25][O:26][CH:22]=3)=[O:34])[C:7](=[O:8])[N:4]2[C:3]=1[C:12]([OH:14])=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

7-Aminodesacetoxycephalosporanic acid (7-amino-3-methylceph-3-em-4-carboxylic acid; 21.4 g., 0.1 mmole) was dissolved in 800 ml. of water by the action of sodium bicarbonate (27.9 g., 0.33 mmole). The solution was diluted with 800 ml. of acetone, and cooled to 0° C. 5-Methyl-3-phenylisoxazole-4-carbonyl chloride (27.7 g., 0.33 mmole) was added and the reaction mixture stirred for 2 hours at 0° C., then held at refrigerator temperature for approximately 16 hours. The acetone was removed by evaporation in vacuo, the aqueous residue extracted several times with ethyl acetate. Layering the aqueous phase with ethyl acetate and adjusting down to 2.0 precipitated the desired product. Filtration with ethyl acetate wash gave 3-methyl-7-(5-methylphenylisoxazole-4-carboxamido)ceph-3-em-4-carboxylic acid [27.5 g., pnmr (TMS/DMSO-d6) delta: includes 2.0 (s, 3H); 2.4 (s, 3H); 3.4 (m, 2H); 7.2-7.8 (m, 5H)].

Workup

additionThe solution was diluted with 800 ml
waitheld at refrigerator temperature for approximately 16 hours
customThe acetone was removed by evaporation in vacuo
extractionthe aqueous residue extracted several times with ethyl acetate
customprecipitated the desired product
filtrationFiltration with ethyl acetate
washwash

Sources & evidence

ORD record: ord-d35f8818b60a41d2994b523f68d478c4
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04429128

Reaction notes

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