Methyl iodide → HCID 20331947, compound
Reaction equation
[C:1]([CH2:6][NH:7][CH2:8][CH2:9][N:10]1[C:14]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[N:13][N:12]=[N:11]1)([O:3][CH2:4][CH3:5])=[O:2].[CH2:25](N(CC)CC)C.CI>O1CCCC1>[C:1]([CH2:6][N:7]([CH3:25])[CH2:8][CH2:9][N:10]1[C:14]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[N:13][N:12]=[N:11]1)([O:3][CH2:4][CH3:5])=[O:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 10 mmol of 1-[2-[[(carbethoxy)-methyl]amino]ethyl]-5-[(4-methoxybenzyl)thio]-1H-tetrazole and 10 mmol of triethylamine in 20 ml. of dry tetrahydrofuran is added 10 mmol of methyliodide. After stirring at room temperature for 24 hours, the mixture is filtered. The filtrate is stripped in vacuo to dryness, and the residue is dissolved in chloroform and chromatographed on silica gel eluting with a gradient of ethylacetate in chloroform. Evaporation of the product-containing fractions gives 1-[2-[[(carbethoxy)methyl]methylamino]ethyl]-5-[(4-methoxy-benzyl)thio]-1H-tetrazole. Deblocking with mercuric acetate as above gives 1-[2-[(carboxymethyl)methylamino]ethyl]-1,4-dihydro-5H-tetrazole-5-thione which when substituted in the reaction with 7-D-mandelamidocephalosporanic acid gives 7-D-mandelamido-3-[1-[2-[(carboxymethyl)methylamino]ethyl]tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid.
Workup
- filtrationthe mixture is filtered
- dissolutionthe residue is dissolved in chloroform
- customchromatographed on silica gel eluting with a gradient of ethylacetate in chloroform
- customEvaporation of the product-containing fractions
Sources & evidence
- ORD record
- ord-a837e77f49c84e1e91739d1343a45e5f
- Source dataset
- uspto-grants-1978_09
- Patent number
- US04117125
Reaction notes
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