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 1074945Notes

Reaction equation

HRID 1074945 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-de985304d0c34747b4355b1c2e4609bb
Source dataset
uspto-grants-1983_07
Patent number
US04394384

Reaction notes

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