Hydrochloric Acid → HCID 131712388, compound

HRID 745709Notes

Reaction equation

HRID 745709 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([CH2:17][O:18][N:19]=[C:20]([C:44]1[N:45]=[C:46]([NH:49]C=O)[S:47][CH:48]=1)[C:21]([NH:23][CH:24]1[C:42](=[O:43])[N:26]2[C:27]([C:39]([OH:41])=[O:40])=[C:28]([CH2:31][S:32][C:33]3[N:37]([CH3:38])[N:36]=[N:35][N:34]=3)[CH2:29][S:30][C@H:25]12)=[O:22])=[O:16])=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.Cl>CO>[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([CH2:17][O:18][N:19]=[C:20]([C:44]1[N:45]=[C:46]([NH2:49])[S:47][CH:48]=1)[C:21]([NH:23][CH:24]1[C:42](=[O:43])[N:26]2[C:27]([C:39]([OH:41])=[O:40])=[C:28]([CH2:31][S:32][C:33]3[N:37]([CH3:38])[N:36]=[N:35][N:34]=3)[CH2:29][S:30][C@H:25]12)=[O:22])=[O:16])([OH:7])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131712389HCID 131712389, compound

Product 1

HCID 131712388HCID 131712388, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

7-[2-{N-(2-tert-Butoxycarbonylphenyl)carbamoylmethoxyimino}-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (2.0 g.) was added to a mixture of trifluoroacetic acid (7 ml.) and anisole (0.35 ml.) with stirring at about 10° C., followed by stirring for 1.5 hours at 5° to 10° C. and for an additional 15 minutes at room temperature. After concentration of the reaction mixture, to the residue were added methanol (30 ml.) and conc. hydrochloric acid (2.33 ml.). The resulting mixture was stirred for 1.5 hours at room temperature and concentrated and then the residue was shaken with a mixture of an aqueous solution of sodium bicarbonate and ethyl acetate. The aqueous layer (pH 7 to 8) was separated and thereto was added ethyl acetate and 10% hydrochloric acid with stirring whereby the pH was adjusted to 2 to 3. The resulting precipitates were filtered and redissolved in an aqueous solution of sodium bicarbonate. To the aqueous solution (150 ml.) was added ethyl acetate (300 ml.) and the mixture was acidified to pH 2 to 3 with 10% hydrochloric acid. The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride, dried and then concentrated. The residue was washed with diethyl ether to give the title compound (0.8 g.). mp. 220° to 230° C. (dec.)

Workup

  1. stirringby stirring for 1.5 hours at 5° to 10° C. and for an additional 15 minutes at room temperature
  2. stirringThe resulting mixture was stirred for 1.5 hours at room temperature
  3. concentrationconcentrated
  4. stirringthe residue was shaken with a mixture of an aqueous solution of sodium bicarbonate and ethyl acetate
  5. customThe aqueous layer (pH 7 to 8) was separated
  6. additionwas added ethyl acetate and 10% hydrochloric acid
  7. stirringwith stirring whereby the pH
  8. customThe resulting precipitates
  9. filtrationwere filtered
  10. dissolutionredissolved in an aqueous solution of sodium bicarbonate
  11. additionTo the aqueous solution (150 ml.) was added ethyl acetate (300 ml.)
  12. customThe ethyl acetate layer was separated
  13. washwashed with an aqueous solution of sodium chloride
  14. customdried
  15. concentrationconcentrated
  16. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-d030d32a08764415b16921c18ddd5693
Source dataset
uspto-grants-1986_07
Patent number
US04599426

Reaction notes

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