Boron trifluoride → HCID 131709915, compound

HRID 1580484Notes

Reaction equation

HRID 1580484 reaction equation
C(O[CH2:5][C:6]1[CH:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:27])[CH:16]([NH:17][C:18](=[O:26])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:9]2[S:8][CH:7]=1)(=O)C.B(F)(F)F.[CH2:32]([O:34][C:35](=O)[CH3:36])C.P([O-])([O-])(O)=O.[K+].[K+]>C1(OC)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:32][O:34][C:35]1[CH:36]=[CH:12][C:11]([CH2:5][C:6]2[CH:11]([C:12]([OH:14])=[O:13])[N:10]3[C:15](=[O:27])[CH:16]([NH:17][C:18](=[O:26])[CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[C@H:9]3[S:8][CH:7]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 6356Boron trifluorideHCID 8857Ethyl AcetateHCID 24450Potassium Phosphate, DibasicHCID 131709916HCID 131709916, compound

Product 1

HCID 131709915HCID 131709915, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 7519AnisoleSolvent

Conditions

Temperature
0 °C

Procedure

0.1 g of 3-acetoxymethyl-7-(N-phenylacetyl-amino)-ceph-2-em-4ξ-carboxylic acid are dissolved in a solution of 0.056 g of anisole in 5 ml of chloroform, and the solution is cooled to 0°C and saturated with boron trifluoride gas for 15 minutes. The temperature of the reaction mixture is thereafter brought to room temperature over the course of 2 hours; 50 ml of acetic acid ethyl ester are added, and the mixture is again cooled to 0°C and slowly poured into 50 ml of a 10% strength aqueous dipotassium hydrogen phosphate solution. The pH value is adjusted to 7.5 and the mixture is thoroughly shaken. The aqueous phase is twice washed with 50 ml portions of acetic acid ethyl ester, the pH value is adjusted to 2 by means of 20% strength aqueous phosphoric acid, and three extractions with 50 ml portions of acetic acid ethyl ester are carried out. The oroganic extracts are repeatedly washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. 3-(4-Methoxy-benzyl)-7-(N-phenylacetyl-amino)-ceph-2-em-4ξ-carboxylic acid containing a small amount of the corresponding 2-methoxy-benzyl compound are thus obtained as the residue; in a thin layer chromatogram, this acid does not differ from the product of the process of example 1.

Workup

  1. customis thereafter brought to room temperature over the course of 2 hours
  2. washThe aqueous phase is twice washed with 50 ml portions of acetic acid ethyl ester
  3. extractionthe pH value is adjusted to 2 by means of 20% strength aqueous phosphoric acid, and three extractions with 50 ml portions of acetic acid ethyl ester
  4. washThe oroganic extracts are repeatedly washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-350a3e0c3d70423fbcad4248af30bbf9
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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