Trifluoroacetic acid → HCID 88823284, compound

HRID 617079Notes

Reaction equation

HRID 617079 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C:16]([O:47][CH3:48])([NH:17][C:18](=[O:46])[C:19](=[N:25][O:26]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C:15](=[O:49])[N:10]2[C:11]=1[C:12]([O-:14])=[O:13])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(=O)(O)[O-].[Na+]>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@@:16]([NH:17][C:18](=[O:46])[C:19](=[N:25][OH:26])[C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)([O:47][CH3:48])[C:15](=[O:49])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131710639HCID 131710639, compound

Product 1

HCID 88823284HCID 88823284, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

t-Butyl (6R,7R and S [ca 1:8])-3-acetoxymethyl-7-methoxy-7[2-triphenylmethoxyimino-2-(thien-2-yl)-acetamido]-ceph-3-em-4-carboxylate (1.172 g, 1.56 mmole) was stirred with anisole (1.5 ml) and trifluoroacetic acid (5 ml) for 1 hour at +20°. The solution was added dropwise to vigorously stirred saturated aqueous sodium bicarbonate solution (400 ml); the mixture was stirred for 10 minutes and then washed with ethyl acetate (3×80 ml). The aqueous layer was covered with ethyl acetate (80 ml) and adjusted to pH 3 with orthophosphoric acid. The aqueous layer was extracted with ethyl acetate (3×80 ml) and the combined ethyl acetate layers were washed with brine, then passed through Whatman 1 PS phase-separating paper and evaporated. The residual foam was chromatographed on kieselgel G (60 g) in 4:1:5 butan-1-ol:ethanol:water. The appropriate fractions were combined and evaporated and the residue was dissolved in acetone, filtered through Celite, and evaporated to provide the title compound as a pale-brown amorphous solid containing 0.8 mole butan-1-ol, and 0.07 mole acetone (nmr) and 5 mole water (416 mg, 0.66 mole, 42.5%), paper chromatography Rf/Rf cephaloram 0.84, [α]D +40° (Me2SO), λmax (pH 6-buffer) 264.5 nm, inflexion at 290 nm (ε 15,200 and 10,700 respectively).

Workup

  1. washwashed with ethyl acetate (3×80 ml)
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×80 ml)
  3. washthe combined ethyl acetate layers were washed with brine
  4. customphase-separating paper
  5. customevaporated
  6. customThe residual foam was chromatographed on kieselgel G (60 g) in 4:1:5 butan-1-ol
  7. customevaporated
  8. dissolutionthe residue was dissolved in acetone
  9. filtrationfiltered through Celite
  10. customevaporated

Sources & evidence

ORD record
ord-9b7ab245207149bf8f4214972848502b
Source dataset
uspto-grants-1978_02
Patent number
US04076936

Reaction notes

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