Potassium Phosphate, Dibasic → HCID 70596888, compound

HRID 224904Notes

Reaction equation

HRID 224904 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[O:14][C:13]([CH2:15][C:16]([OH:18])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(Cl)=O)C(C)C.[C:27]1([CH:33]([O:40][C:41]([C:43]2[N:48]3[C:49](=[O:52])[C@@H:50]([NH2:51])[C@H:47]3[S:46][CH2:45][C:44]=2[CH2:53][O:54][C:55](=[O:57])[CH3:56])=[O:42])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.P([O-])([O-])(O)=O.[K+].[K+]>C(Cl)Cl.CN1CCOCC1.O>[C:27]1([CH:33]([O:40][C:41]([C:43]2[N:48]3[C:49](=[O:52])[C@@H:50]([NH:51][C:16](=[O:18])[CH2:15][C:13]4[O:14][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:11][CH:12]=4)[C@H:47]3[S:46][CH2:45][C:44]=2[CH2:53][O:54][C:55](=[O:57])[CH3:56])=[O:42])[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 24450Potassium Phosphate, DibasicHCID 62365Isobutyl chloroformateHCID 10575011HCID 10575011, compoundHCID 23330365HCID 23330365, compound

Product 1

HCID 70596888HCID 70596888, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 79724-MethylmorpholineSolvent

Conditions

Temperature
-20 °C

Procedure

1.87 g of 2-(5-tert.-butoxycarbonylaminomethyl-2-furyl)-acetic acid are dissolved in 200 ml of methylene chloride (distilled over phosphorus pentoxide) and 0.80 ml of 4-methylmorpholine, the solution, from which moisture is kept excluded, is cooled to -20° C. and 1.0 ml of chloroformic acid isobutyl ester is added dropwise whilst keeping the temperature at between -15° C. and -20° C. After 30 minutes, a solution of 2.31 g of 3-acetoxymethyl-7β-amino-3-cephem-4-carboxylic acid diphenylmethyl ester is added, after which the mixture is stirred for a further 2 hours at -10° C. and for 8 hours at room temperature. It is then poured out into icecold water, the pH is adjusted to 8.0 with dipotassium hydrogen phosphate and the mixture is repeatedly extracted with methylene chloride. The organic extracts are washed with a saturated aqueous sodium chloride solution and dried over magnesium sulphate, after which the solvent is removed under reduced pressure. 3-Acetoxymethyl-7β-[2-(5-tert.-butoxycarbonylaminomethyl-2-furyl)-acetylamino]-3-cephem-4-carboxylic acid diphenylmethyl ester is obtained as a colourless foam which is directly converted further; thin layer chromatogram (silica gel): Rf=0.84 (system: hexane/ethyl acetate/methanol, 20:40:40).

Workup

  1. customat between -15° C. and -20° C
  2. extractionthe mixture is repeatedly extracted with methylene chloride
  3. washThe organic extracts are washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customafter which the solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-463db412096b46d6bb500fb4ed2e62a2
Source dataset
uspto-grants-1980_11
Patent number
US04234578

Reaction notes

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