Phenol → HCID 131709918, compound

HRID 1580483Notes

Reaction equation

HRID 1580483 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.[C:28]1([OH:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>[OH:34][C:28]1[CH:33]=[CH:32][C:31]([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:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C@H:9]3[S:8][CH:7]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 996PhenolHCID 131709916HCID 131709916, compound

Product 1

HCID 131709918HCID 131709918, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1.95 g of 3-acetoxymethyl-7-(N-phenylacetyl-amino)-ceph-2-em-4ξ-carboxylic acid are dissolved in a solution of 4.7 g of phenol in 15 ml of trifluoroacetic acid, and the solution is left to stand for 15 minutes at room temperature and is then diluted with an equal amount of toluene. After evaporation under reduced pressure, the residue is taken up in 100 ml of acetic acid ethyl ester and 50 ml of an aqueous 10% strength dipotassium hydrogen phosphate solution, the mixture is well shaken and the organic phase is separated off. The aqueous layer is twice washed with 100 ml portions of acetic acid ethyl ester to remove the excess phenol and then covered with 100 ml of acetic acid ethyl ester, and its pH value is adjusted to 2 by means of 20% strength aqueous phosphonic acid. The organic layer is separated off after thorough shaking, the aqueous solution is twice extracted with 100 ml portions of acetic acid ethyl ester, and the combined organic extracts are washed three times with 50 ml portions of a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate, filtered and evaporated to dryness under reduced pressure. The residue is triturated with acetic acid ethyl ester and yields 3-(4-hydroxy-benzyl)-7-(N-phenylacetyl-amino)-ceph-2-em-4ξ-carboxylic acid, which after recrystallisation from a mixture of acetic acid ethyl ester and methanol melts at 210°C; thin layer chromatogram (silica gel): Rf = 0.72 (system n-butanol/acetic acid/water, 75:7.5:21), Rf = 0.77 (system n-butanol/acetic acid/water, 67:10:23) and Rf = 0.49 (system n-butanol/ethanol/water, 40:10:50); ultraviolet absorption spectrum (in methanol): λmax = 224 mμ (ε = 15800) and 276 mμ (ε = 2400), and shoulder at 282 mμ (ε = 1900); infrared absorption spectrum (in mineral oil): characteristic bands at 3.01μ, 5.77μ, 5.80μ, 6.07μ and 6.62μ.

Workup

  1. waitthe solution is left
  2. customAfter evaporation under reduced pressure
  3. customthe organic phase is separated off
  4. washThe aqueous layer is twice washed with 100 ml portions of acetic acid ethyl ester
  5. customto remove the excess phenol
  6. customThe organic layer is separated off after thorough shaking
  7. extractionthe aqueous solution is twice extracted with 100 ml portions of acetic acid ethyl ester
  8. washthe combined organic extracts are washed three times with 50 ml portions of a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulphate
  10. filtrationfiltered
  11. customevaporated to dryness under reduced pressure
  12. customThe residue is triturated with acetic acid ethyl ester

Sources & evidence

ORD record
ord-1f193e2193db4bb6838b3a61b894cb02
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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