Hydrochloric Acid → HCID 131710692, compound

HRID 597161Notes

Reaction equation

HRID 597161 reaction equation
Cl.[C:2]([O:5][CH2:6][C:7]1[C@H:12]([C:13]([OH:15])=[O:14])[N:11]2[C:16](=[O:19])[C@@H:17]([NH2:18])[C@H:10]2[S:9][CH:8]=1)(=[O:4])[CH3:3].C[Si](C)(C)N[Si](C)(C)C.[Cl:29][C:30]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:31]=1[C:32](Cl)=[O:33].C(C(CCCC)C([O-])=O)C.[Na+:50]>C(OCC)(=O)C.C(Cl)(Cl)Cl>[C:2]([O:5][CH2:6][C:7]1[C@H:12]([C:13]([O-:15])=[O:14])[N:11]2[C:16](=[O:19])[C@@H:17]([NH:18][C:32](=[O:33])[C:31]3[C:30]([Cl:29])=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:39])[C@H:10]2[S:9][CH:8]=1)(=[O:4])[CH3:3].[Na+:50]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 13838HexamethyldisilazaneHCID 783922,6-Dichlorobenzoyl chlorideHCID 23672331Sodium 2-ethylhexanoateHCID 131710691HCID 131710691, compound

Product 1

HCID 131710692HCID 131710692, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

The hydrochloride of 3-acetoxymethyl-7β-aminoceph-2-em-4α-carboxylic acid (1.5 g., 0.05 m.mol) was heated in refluxing dry chloroform (20 ml) containing hexamethyldisilazane (3.2 ml. 0.015 mol) for 1 hr. The excess silylating reagent and solvent were removed under high vacuum. The resulting gum was redissolved in dry ethyl acetate (20 ml) and 2,6-dichlorobenzoyl chloride (1.0 g 0.45 mmol) added. the reaction was carried out for 1 hr. at reflux. Treatment of the organic phase with dilute hydrochloric acid, water, drying and evaporation gave a gum. Addition of a solution of 10% sodium 2-ethylhexanoate in ethyl acetate precipitated a sodium salt, νmax (Nujol) 3300 (NH), 1760 (β-lactam), 1720 (acetate), 1660 (amide) and 1605 cm-1 (--CO2Na), RF (system 3) 0.53 (with an impurity, RF 0.19). These properties are consistent with the structure of the compound named in the title.

Workup

  1. customThe excess silylating reagent and solvent were removed under high vacuum
  2. dissolutionThe resulting gum was redissolved in dry ethyl acetate (20 ml)
  3. temperatureat reflux
  4. dry with materialTreatment of the organic phase with dilute hydrochloric acid, water, drying
  5. customevaporation
  6. customgave a gum
  7. customprecipitated a sodium salt, νmax (Nujol) 3300 (NH), 1760 (β-lactam), 1720 (acetate), 1660 (amide) and 1605 cm-1 (--CO2Na), RF (system 3) 0.53 (with an impurity, RF 0.19)

Sources & evidence

ORD record
ord-533efd64372b4a8fa8abb9820891b292
Source dataset
uspto-grants-1977_03
Patent number
US04013645

Reaction notes

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