Hydrochloric Acid → 3-[1-(2-carboxyethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

HRID 1577749Notes

Reaction equation

HRID 1577749 reaction equation
O.O.O.C([O-])(=O)C.[Na+].C(ON=C(C1N=C(NC(=O)C(F)(F)F)SC=1)C(N[CH:18]1[C:40](=[O:41])[N:20]2[C:21]([C:37]([OH:39])=[O:38])=[C:22]([CH2:25][S:26][C:27]3[N:31]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])[N:30]=[N:29][N:28]=3)[CH2:23][S:24][C@H:19]12)=O)C#C.Cl>O>[C:34]([CH2:33][CH2:32][N:31]1[C:27]([S:26][CH2:25][C:22]2[CH2:23][S:24][C@@H:19]3[CH2:18][C:40](=[O:41])[N:20]3[C:21]=2[C:37]([OH:39])=[O:38])=[N:28][N:29]=[N:30]1)([OH:36])=[O:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665404Sodium Acetate TrihydrateHCID 1317124097-[2-(2-propynyloxyimino)-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-[1-(2-carboxyethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317124103-[1-(2-carboxyethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acidYield 111.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium acetate trihydrate (5.97 g) in water (25 ml) was added to 7-[2-(2-propynyloxyimino)-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-[1-(2-carboxyethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(3.0 g) and the mixture was stirred overnight. The reaction mixture was adjusted to pH 3 with 10% hydrochloric acid under ice-cooling and precipitates were collected by filtration, washed with water and dried to give 7-[2-propynyloxyimino)-2-(2-aminothiazol-4-yl)acetamido]-3-[1-(2-carboxyethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.80 g).

Workup

  1. temperaturecooling
  2. customprecipitates
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-8f672a0086c54f54bc102f65934694a5
Source dataset
uspto-grants-1981_09
Patent number
US04288436

Reaction notes

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