Sodium Iodide → HCID 70507474, compound

HRID 1702737Notes

Reaction equation

HRID 1702737 reaction equation
[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[CH:12]([NH:13][C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:18][O:19][C:20]=3[CH3:21])=[O:15])[C:11](=[O:28])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].C(N(CC)CC)C.C(=O)(O)[O-].[K+].[I-].[Na+].[C:43]([O:49][CH2:50]Cl)(=[O:48])[C:44]([CH3:47])([CH3:46])[CH3:45]>CN(C)C=O.C(OCC)(=O)C.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[CH:12]([NH:13][C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:18][O:19][C:20]=3[CH3:21])=[O:15])[C:11](=[O:28])[N:6]2[C:7]=1[C:8]([O:10][CH2:50][O:49][C:43](=[O:48])[C:44]([CH3:47])([CH3:46])[CH3:45])=[O:9]

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 87885Chloromethyl pivalate2×HCID 516893Potassium BicarbonateHCID 70508451HCID 70508451, compound

Product 1

HCID 70507474HCID 70507474, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methyl-7-(5-methyl-3-phenylisoxazole-4-carboxamido)ceph-3-em-4-carboxylic acid (25.9 g., 65 mmoles) was dissolved in anhydrous dimethylformamide (150 ml.). Triethylamine (19.7 g., 195 mmoles), potassium bicarbonate (19.5 g., 195 mmoles), sodium iodide (29.3 g., 195 mmoles) and chloromethyl pivalate (29.3 g., 195 mmoles) were added. An exotherm was noted, the temperature rising to approximately 35° C. After stirring for 6 hours at ambient temperature, monitoring by tlc (4:1 chloroform:ethyl acetate) indicated considerable starting material remained. Additional chloromethyl pivalate (8.4 g., 65 mmoles) was added and stirring at ambient temperature continued for 16 hours. Isolation as detailed in Preparation 1 gave pivaloyloxymethyl 3-methyl-7-(5-methyl-3-phenylisoxazole-4-carboxamido)ceph-3-em-4-carboxylate [25.3 g., 76%; Rf 0.8 (4:1 chloroform:ethyl acetate; ir (CH2Cl2) 1780, 1750, 1670 cm-1 ].

Workup

  1. customrising to approximately 35° C
  2. stirringstirring at ambient temperature
  3. waitcontinued for 16 hours
  4. customIsolation as detailed in Preparation 1

Sources & evidence

ORD record
ord-fccb5c387c084bb3950344dabe50851e
Source dataset
uspto-grants-1982_09
Patent number
US04348264

Reaction notes

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