Tetrahydrofuran → 7-[2-(2-Aminothiazol-4-yl)-2-(2,4-dichlorobenzyloxyimino)-acetamido]-3-cephem-4-carboxylic acid

HRID 894813Notes

Reaction equation

HRID 894813 reaction equation
FC(F)(F)C([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Cl:37])[C:12]([NH:14][CH:15]2[C:25](=[O:26])[N:17]3[C:18]([C:22]([OH:24])=[O:23])=[CH:19][CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1)=O.O1CCCC1.C([O-])(=O)C.[Na+].C(OCC)(=O)C>O>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Cl:37])[C:12]([NH:14][CH:15]2[C:25](=[O:26])[N:17]3[C:18]([C:22]([OH:24])=[O:23])=[CH:19][CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 131712357HCID 131712357, compound

Product 1

HCID 1317123567-[2-(2-Aminothiazol-4-yl)-2-(2,4-dichlorobenzyloxyimino)-acetamido]-3-cephem-4-carboxylic acidYield 17.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

7-[2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]-2-(2,4-dichlorobenzyloxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 2.0 g.) and tetrahydrofuran (30 ml.) were added to a solution of sodium acetate (4.6 g.) in water (100 ml.), and then the mixture was stirred at room temperature for 5 days. Ethyl acetate and water were added to the reaction mixture, and the aqueous layer was separated. Ethyl acetate and tetrahydrofuran were added to the aqueous solution and adjusted to pH 6.2 with 10% hydrochloric acid. The aqueous layer was separated and adjusted to pH 3.0 with 10% hydrochloric acid. The precipitates were collected by filtration, washed with water and dried to give 7-[2-(2-aminothiazol-4-yl)-2-(2,4-dichlorobenzyloxyimino)-acetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.3 g.). m.p. 167° to 193° C. (dec.).

Workup

  1. customthe aqueous layer was separated
  2. additionEthyl acetate and tetrahydrofuran were added to the aqueous solution
  3. customThe aqueous layer was separated
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ab9622363a1d48a9b0aecdc42423f93a
Source dataset
uspto-grants-1981_08
Patent number
US04284631

Reaction notes

Loading…