Hydrochloric Acid → 7-[2-(2-Cyclopenten-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(tetrazolo[1,5-b] pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 371248Notes

Reaction equation

HRID 371248 reaction equation
[CH:1]1([O:6][N:7]=[C:8]([C:35]2[N:36]=[C:37]([NH:40]C=O)[S:38][CH:39]=2)[C:9]([NH:11][CH:12]2[C:33](=[O:34])[N:14]3[C:15]([C:30]([OH:32])=[O:31])=[C:16]([CH2:19][S:20][C:21]4[CH:22]=[CH:23][C:24]5[N:25]([N:27]=[N:28][N:29]=5)[N:26]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1.Cl.O1CCCC1.C(=O)(O)[O-].[Na+]>CO.O.C(OCC)(=O)C>[CH:1]1([O:6][N:7]=[C:8]([C:35]2[N:36]=[C:37]([NH2:40])[S:38][CH:39]=2)[C:9]([NH:11][CH:12]2[C:33](=[O:34])[N:14]3[C:15]([C:30]([OH:32])=[O:31])=[C:16]([CH2:19][S:20][C:21]4[CH:22]=[CH:23][C:24]5[N:25]([N:27]=[N:28][N:29]=5)[N:26]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 516892Sodium Bicarbonate2×HCID 1317130267-[2-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317130357-[2-(2-Cyclopenten-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(tetrazolo[1,5-b] pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acidYield 61.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(1.7 g) in methanol (12.0 ml) and conc.hydrochloric acid (0.56 g) was stirred and then thereto was added tetrahydrofuran (12.0 ml) to give a homogenous solution, which was stirred for 2 hours and 50 minutes at room temperature. To the reaction mixture were added water and sodium bicarbonate so that the pH was adjusted to 5.0. After the concentration of the mixture, to the concentrate were added ethyl acetate, water and sodium bicarbonate so that the pH was adjusted to 7.5. The aqueous layer was separated, washed with ethyl acetate (×2), concentrated and adjusted to pH 3.0 with 10% hydrochloric acid. The precipitates were collected by filtration, washed with water, dried over phosphorus pentoxide under reduced pressure to give 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(tetrazolo[1,5-b]pyridazin- 6-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(1.00 g). mp. 178° to 180° C. (dec.).

Workup

  1. customto give a homogenous solution, which
  2. customThe aqueous layer was separated
  3. washwashed with ethyl acetate (×2)
  4. concentrationconcentrated and adjusted to pH 3.0 with 10% hydrochloric acid
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water
  7. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-2e0286e34d6f49daa950b62844fa2825
Source dataset
uspto-grants-1985_07
Patent number
US04529802

Reaction notes

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