4-Methylthiazole-5-carboxaldehyde → HCID 131715960, compound

HRID 1904646Notes

Reaction equation

HRID 1904646 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:55](=[O:56])[N:14]2[C:15]([C:39]([O:41][CH:42]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:40])=[C:16]([CH:19]=P(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:57][C:58]1[N:59]=[CH:60][S:61][C:62]=1[CH:63]=O>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH:42]([O:41][C:39]([C:15]1[N:14]2[C:55](=[O:56])[CH:12]([NH:11][C:9](=[O:10])[CH2:8][O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@H:13]2[S:18][CH2:17][C:16]=1[CH:19]=[CH:63][C:62]1[S:61][CH:60]=[N:59][C:58]=1[CH3:57])=[O:40])([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

5

Reactant 2

HCID 5813394-Methylthiazole-5-carboxaldehydeHCID 13728347HCID 13728347, compound

Product 1

HCID 131715960HCID 131715960, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Benzhydryl 7-(phenoxyacetamido)-3-(triphenylphosphoran-diylmethyl)-3-cephem-4-carboxylate (1.55 g ) and 4-methylthiazol-5-carboaldehyde (0.305 g) were dissolved in methylene chloride (20 ml), to which aqueous saturated sodium bicarbonate (20 ml) was added at ambient temperature. The resultant mixture was stirred for 17 hours at ambient temperature. The mixture was allowed to stand until it separated into the aqueous phase and organic solvent phase. The aqueous phase was removed and washed with methylene chloride (20 ml), and the washings (in methylene chloride) were combined with the organic solvent phase separated. The combined solution was dried over anhydrous magnesium sulfate and then concentrated to dryness under reduced pressure. The solid residue obtained was purified chromatographically on a column of silica gel (Wako gel C-300) (40 g) as developed with benzene-ethyl acetate (5:1) as the development solvent. The entitled compound, 7-(phenoxyacetamido)-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid benzhydryl ester (0.741 g) was obtained.

Workup

  1. additionwas added at ambient temperature
  2. customseparated into the aqueous phase and organic solvent phase
  3. customThe aqueous phase was removed
  4. washwashed with methylene chloride (20 ml)
  5. customseparated
  6. dry with materialThe combined solution was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe solid residue obtained
  9. customwas purified chromatographically on a column of silica gel (Wako gel C-300) (40 g)

Sources & evidence

ORD record
ord-16297abe600c43329e6363dcb7550ef5
Source dataset
uspto-grants-1989_06
Patent number
US04839350

Reaction notes

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