Hydrochloric Acid → HCID 131713036, compound

HRID 1074946Notes

Reaction equation

HRID 1074946 reaction equation
[CH:1]1([O:6][N:7]=[C:8]([C:42]2[N:43]=[C:44]([NH:47]C=O)[S:45][CH:46]=2)[C:9]([NH:11][CH:12]2[C:40](=[O:41])[N:14]3[C:15]([C:37]([OH:39])=[O:38])=[C:16]([CH2:19][S:20][C:21]4[N:25]([CH2:26][CH2:27][CH2:28][NH:29]C(OC(C)(C)C)=O)[N:24]=[N:23][N:22]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1.Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>CO.O>[CH:1]1([O:6][N:7]=[C:8]([C:42]2[N:43]=[C:44]([NH2:47])[S:45][CH:46]=2)[C:9]([NH:11][CH:12]2[C:40](=[O:41])[N:14]3[C:15]([C:37]([OH:39])=[O:38])=[C:16]([CH2:19][S:20][C:21]4[N:25]([CH2:26][CH2:27][CH2:28][NH2:29])[N:24]=[N:23][N:22]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 131713037HCID 131713037, compound

Product 1

HCID 131713036HCID 131713036, compoundYield 21.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[1-[3-(N-tertbutoxycarbonylamino)propyl]-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.75 g) in methanol (13 ml) was added conc.hydrochloric acid (1.0 g) with stirring and the mixture was stirred for 3 hours at room temperature. After the evaporation of the resulting mixture, to the residue was added methanol (20 ml) to give a homogeneous solution and then the solution was evaporated. Solution and evaporation were repeated three times and to the resulting reaction mixture were added ethyl acetate and water. After the mixture was adjusted to pH 7.5 with sodium bicarbonate, the aqueous layer was separated, washed with ethyl acetate and the remaining ethyl acetate was distilled off. The resulting aqueous layer was adjusted to pH 3.8 with 1 N hydrochloric acid and then filtered. The precipitates thus collected were washed with water and dried over phosphorus pentoxide under reduced pressure to give 7-[2-(2-cyclopenten- 1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[1-(3-aminopropyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(0.31 g).

Workup

  1. customAfter the evaporation of the resulting mixture
  2. additionto the residue was added methanol (20 ml)
  3. customto give a homogeneous solution
  4. customthe solution was evaporated
  5. customSolution and evaporation
  6. customto the resulting reaction mixture
  7. customthe aqueous layer was separated
  8. washwashed with ethyl acetate
  9. distillationthe remaining ethyl acetate was distilled off
  10. filtrationfiltered
  11. customThe precipitates thus
  12. customcollected
  13. washwere washed with water
  14. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-628c2cad51f84c889cce0bda68ffe6d5
Source dataset
uspto-grants-1983_07
Patent number
US04394384

Reaction notes

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