Potassium Carbonate → p-Methoxybenzyl 3-methyl-7beta-phenoxyacetamidoceph-3-em-4-carboxylate

HRID 1657396Notes

Reaction equation

HRID 1657396 reaction equation
[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[C@H:12]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11](=[O:24])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]N)=[CH:29][CH:28]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].N(Cl)=O>ClCCl>[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[C@H:12]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11](=[O:24])[N:6]2[C:7]=1[C:8]([O:10][CH2:31][C:30]1[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=1)=[O:9]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 17601Nitrosyl chlorideHCID 24436Sodium SulfateHCID 754524-MethoxybenzylamineHCID 111318273-Methyl-7beta-phenoxyacetamidoceph-3-em-4-carboxylic acid

Product 1

HCID 68133766p-Methoxybenzyl 3-methyl-7beta-phenoxyacetamidoceph-3-em-4-carboxylateYield 50.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methyl-7β-phenoxyacetamidoceph-3-em-4-carboxylic acid (3.48 g., 10 m. moles) was dissolved in dichloromethane (50 ml) with p-methoxy-benzylamine (3.43 g., 25 m. moles) together with anhydrous sodium sulphate (5 g) and potassium carbonate (6.7 g). Nitrosyl chloride (12.5 ml, 10% solution in dichloromethane, 25 m. moles) was added over about 10 minutes at -5° with vigorous stirring. Some partial gel formation occurred but this dissolved while the mixture was stirred for a further 50 minutes while warming towards ambient. The reaction mixture was worked up as described in Example 7 and the organic residue crystallised from hot isopropanol (25 ml) to give the title compound (2.38 g., 50.6% yield based on the input acid) m.pt. 151° - 152°.

Workup

  1. dissolutionthis dissolved while the mixture
  2. temperaturewhile warming towards ambient
  3. customthe organic residue crystallised from hot isopropanol (25 ml)

Sources & evidence

ORD record
ord-9dfd52991c85483bb5685b45976c9899
Source dataset
uspto-grants-1976_06
Patent number
US03960843

Reaction notes

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