Trifluoroacetic acid → HCID 131709938, compound

HRID 1580502Notes

Reaction equation

HRID 1580502 reaction equation
C1(C([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:34])[C@@H:24]([C:25](=[O:33])[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@H:21]3[S:20][C:19]([NH2:35])=[C:18]2[CH2:36][C:37]2[O:41][C:40]([C:42]([O:44]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:43])=[CH:39][CH:38]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[C:42]([C:40]1[O:41][C:37]([CH2:36][C:18]2[CH:17]([C:15]([OH:16])=[O:14])[N:22]3[C:23](=[O:34])[C@@H:24]([C:25](=[O:33])[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@H:21]3[S:20][C:19]=2[NH2:35])=[CH:38][CH:39]=1)([OH:44])=[O:43]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131709939HCID 131709939, compound

Product 1

HCID 131709938HCID 131709938, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.550 g of 3-(5-diphenylmethoxycarbonyl-furfuryl)-7β-phenylacetyl-amino-ceph-2-em-4ξ-carboxylic acid diphenylmethyl ester and 0.380 g of anisol is treated with 10 ml of trifluoroacetic acid and left to stand for 10 minutes at room temperature. The mixture is diluted with an equal volume of toluene and evaporated under reduced pressure. The residue is partitioned between ethyl acetate and a 10% aqueous dipotassium hydrogen phosphate solution (pH 7.8). The layers are separated, the aqueous phase is washed several times with ethyl acetate and the pH adjusted to 2.5 by addition of 20% aqueous phosphoric acid. After extraction with ethyl acetate, the resulting organic extracts are washed with water and a saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated under reduced pressure. The residue is recrystallised from ethyl acetate and yields the 3-(5-carboxy-furfuryl)-7β-phenylacetyl-amino-ceph-2-em-4ξ-carboxylic acid, which melts at 194°-195°; [α]D20 = + 315° ± 1° (c = 1.010 in dioxan): thin-layer chromatogram (silica gel): Rf = 0.65 (system n-butanol/acetic acid/water 67:10:23) and Rf = 0.38 (system n-butanol/ethanol/water 40:10:50); infrared absorption spectrum (in mineral oil): characteristic bands at 2,99μ, 5,67μ, 5,76μ, 5,90μ, 6,04μ, 6,26μ, 6,51μ and 6,53μ (shoulder).

Workup

  1. waitleft
  2. customevaporated under reduced pressure
  3. customThe residue is partitioned between ethyl acetate
  4. customThe layers are separated
  5. washthe aqueous phase is washed several times with ethyl acetate
  6. additionthe pH adjusted to 2.5 by addition of 20% aqueous phosphoric acid
  7. extractionAfter extraction with ethyl acetate
  8. washthe resulting organic extracts are washed with water
  9. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulphate
  10. customevaporated under reduced pressure
  11. customThe residue is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-66ab518901b94a5e90e44d7f4963474f
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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