Guaiacol → HCID 131709926, compound

HRID 1580493Notes

Reaction equation

HRID 1580493 reaction equation
C(O[CH2:5][C:6]1[CH:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:26])[C@@H:16]([C:17](=[O:25])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@H:9]2[S:8][C:7]=1[NH2:27])(=O)C.[C:28]1([O:35][CH3:36])[C:29](=[CH:31][CH:32]=[CH:33][CH:34]=1)[OH:30]>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>[OH:30][C:29]1[CH:31]=[CH:32][C:33]([CH2:5][C:6]2[CH:11]([C:12]([OH:14])=[O:13])[N:10]3[C:15](=[O:26])[C@@H:16]([C:17](=[O:25])[CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C@H:9]3[S:8][C:7]=2[NH2:27])=[CH:34][C:28]=1[O:35][CH3:36]

Participants

5

Reactant 2

HCID 460GuaiacolHCID 131709927HCID 131709927, compound

Product 1

HCID 131709926HCID 131709926, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

11.7 Grams of 3-acetyloxymethyl-7β-phenylacetyl-amino-ceph-2-em-4ξ-carboxylic acid are dissolved in a solution of 18.6 g of guaiacol in 300 ml of trifluoroacetic acid and the mixture is left to stand to 15 minutes at room temperature, then diluted with an equal volume of toluene and evaporated under reduced pressure. The residue is partitioned between ethyl acetate and an aqueous dipotassium hydrogen phosphate buffer solution (pH 7.5) and the layers are separated. The aqueous layer is thoroughly washed with ethyl acetate, its pH then adjusted to 2.5 with 20% aqueous phosphoric acid and again extracted with ethyl acetate. The latter extracts are washed with water and a saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated under reduced pressure. The residue is recrystallised from ethyl acetate to yield the 3-(4-hydroxy-3-methoxy-benzyl)-7β-phenylacetyl-amino-ceph-2-em-4ξ-carboxylic acid, m.p. 198-199°; thin-layer chromatogram (silica gel): Rf = 0.76 (system n-butanol/acetic acid/water 67:10:23) and Rf = 0.43 (system n-butanol/ethanol/water 40:10:50); ultraviolet absorption spectrum (in methanol): λmax = 235 mμ (ε = 6800) and 282 mμ (ε = 1820); infrared absorption spectrum (in mineral oil): characteristic bands at 2,85μ, 2,99μ, 5,67μ, 5.74μ and 6.56μ. It is possible to obtain a further amount of the desired product from the mother liquor via the diphenylmethyl ester.

Workup

  1. waitthe mixture is left
  2. customevaporated under reduced pressure
  3. customThe residue is partitioned between ethyl acetate
  4. customan aqueous dipotassium hydrogen phosphate buffer solution (pH 7.5) and the layers are separated
  5. washThe aqueous layer is thoroughly washed with ethyl acetate, its pH
  6. extractionagain extracted with ethyl acetate
  7. washThe latter extracts are washed with water
  8. dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulphate
  9. customevaporated under reduced pressure
  10. customThe residue is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-c4ba6d6113df44f1bf6bed10755b0a98
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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