Sodium Bicarbonate → 7beta-[2-(2-Amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 126903Notes

Reaction equation

HRID 126903 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:49])[C@@H:24]([NH:25][C:26](=[O:48])[C:27]([C:31]4[N:32]=[C:33]([NH:37]C(OCC5C=CC=CC=5)=O)[S:34][C:35]=4[Cl:36])=[N:28][O:29][CH3:30])[C@H:21]3[S:20][CH2:19][CH:18]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].C(=O)([O-])O.[Na+]>C1(OC)C=CC=CC=1>[NH2:37][C:33]1[S:34][C:35]([Cl:36])=[C:31]([C:27](=[N:28][O:29][CH3:30])[C:26]([NH:25][C@@H:24]2[C:23](=[O:49])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[CH:18][CH2:19][S:20][C@H:21]23)=[O:48])[N:32]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 1317121077beta-[2-(2-Carbobenzoxyamino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester

Product 1

HCID 1317121027beta-[2-(2-Amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acidYield 74%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 7β-[2-(2-carbobenzoxyamino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester (216 mg) in anisole (5 ml) is added aluminium chloride (400 mg) under ice-cooling, and the mixture is stirred for 90 minutes at 10° C. The reaction mixture is adjusted to pH 8-9 with 5% aqueous sodium hydrogen carbonate solution, and filtered to remove separated solid. The filtrate is washed with ethyl acetate, acidified with 10% hydrochloric acid to pH 2 and extracted with methyl ethyl ketone. The extract solution is washed with saline, dried over sodium sulfate and concentrated. The obtained residue is solidified with ether, collected by filtration, and washed with ether to give 7β-[2-(2-amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (93 mg). Yield: 74%.

Workup

  1. temperaturecooling
  2. filtrationfiltered
  3. customto remove
  4. customseparated solid
  5. washThe filtrate is washed with ethyl acetate
  6. extractionextracted with methyl ethyl ketone
  7. washThe extract solution is washed with saline
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. filtrationcollected by filtration
  11. washwashed with ether

Sources & evidence

ORD record
ord-01656c1879ab42d8ac8c95c6abaa1100
Source dataset
uspto-grants-1981_03
Patent number
US04254119

Reaction notes

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