Hydrochloric Acid → HCID 131713036, compound

HRID 371249Notes

Reaction equation

HRID 371249 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 1N 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. stirringthe mixture was stirred for 3 hours at room temperature
  2. customAfter the evaporation of the resulting mixture
  3. additionto the residue was added methanol (20 ml)
  4. customto give a homogeneous solution
  5. customthe solution was evaporated
  6. customSolution and evaporation
  7. customto the resulting reaction mixture
  8. customthe aqueous layer was separated
  9. washwashed with ethyl acetate
  10. distillationthe remaining ethyl acetate was distilled off
  11. filtrationfiltered
  12. customThe precipitates thus
  13. customcollected
  14. washwere washed with water
  15. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-f6b4fa2c1c1043dca8e21efac48785a8
Source dataset
uspto-grants-1985_07
Patent number
US04529802

Reaction notes

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