Diisopropyl Ether → HCID 131715961, compound

HRID 1904647Notes

Reaction equation

HRID 1904647 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:43](=[O:44])[N:14]2[C:15]([C:27]([O:29]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:28])=[C:16]([CH:19]=[CH:20][C:21]3[S:25][CH:24]=[N:23][C:22]=3[CH3:26])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(C)C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:43](=[O:44])[N:14]2[C:15]([C:27]([OH:29])=[O:28])=[C:16]([CH:19]=[CH:20][C:21]3[S:25][CH:24]=[N:23][C:22]=3[CH3:26])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7914Diisopropyl Ether2×HCID 131715960HCID 131715960, compound

Product 1

HCID 131715961HCID 131715961, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

Benzhydryl 7-(phenoxyacetamido)-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylate (0.725 g) was dissolved in anisole (2 ml), to which trifluoroacetic acid (7 ml) was added under ice-cooling. The mixture was stirred for 1 hour under ice-cooling. The reaction mixture was concentrated under reduced pressure to give a syrup, whcih was then solidified by addition of isopropyl ether thereto. The solid obtained was pulverized and was mixed with isopropyl ether for the washing purpose, and the mixture was filtered to recover the solid which was then dried under reduced presssure. 7-(Phenoxyacetamido)-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid (0.512 g) was thus obtained.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperaturecooling
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customto give a syrup, whcih
  6. customThe solid obtained
  7. filtrationthe mixture was filtered
  8. customto recover the solid which
  9. customwas then dried

Sources & evidence

ORD record
ord-fa6d70c800c540dea022183d672b6821
Source dataset
uspto-grants-1989_06
Patent number
US04839350

Reaction notes

Loading…