Water → HCID 131712824, compound

HRID 1702736Notes

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-a8a4f747693e4e7aaf9b2387329d8e76
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04348264

Reaction notes

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