Formic Acid → HCID 178512425, compound

HRID 1073826Notes

Reaction equation

HRID 1073826 reaction equation
O[CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:13]([NH:14][C:15](=[O:63])/[C:16](/[C:38]3[N:39]=[C:40]([NH:43]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:41][CH:42]=3)=[N:17]\[O:18]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:12](=[O:64])[N:7]2[C:8]=1[C:9]([O-:11])=[O:10].[Na+].[C:66]([CH2:69][S:70][C:71]1[N:75]=[C:74]([SH:76])[S:73][N:72]=1)(=[NH:68])[NH2:67].C(O)=O>CN(C=O)C>[C:66]([CH2:69][S:70][C:71]1[N:75]=[C:74]([S:76][CH2:2][C:3]2[CH2:4][S:5][C@@H:6]3[C@H:13]([NH:14][C:15](=[O:63])/[C:16](/[C:38]4[N:39]=[C:40]([NH2:43])[S:41][CH:42]=4)=[N:17]\[OH:18])[C:12](=[O:64])[N:7]3[C:8]=2[C:9]([OH:11])=[O:10])[S:73][N:72]=1)(=[NH:67])[NH2:68]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 23676286sodium (6R,7R)-3-(hydroxymethyl)-8-oxo-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 178512426HCID 178512426, compound

Product 1

HCID 178512425HCID 178512425, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 909 mg of sodium 3-hydroxymethyl-7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-trityloxyiminoacetamido]-3-cephem-4-carboxylate and 619 mg of 3-amidino methylthio-5-mercapto-1,2,4-thiadiazole in 8 ml of DMF was added 1.4 g of ethyl o-phenylenephosphate under ice-cooling and stirring. The reaction mixture was stirred at room temperature for 4 hours and then subjected to a column chromatography on silica gel (150 g), being eluted with aceton/water (95:5). The eluate was concentrated to dryness under reduced pressure to obtain a powder to which was added 20 ml of formic acid. After stirring at room temperature for 14 hours, the mixture was distilled under reduced pressure to remove formic acid. The residue was added with water and THF, adjusted to pH 7 under ice-cooling, washed with ethyl acetate, concentrated under reduced pressure and then subjected to a column chromatography on XAD-II (140 mg), being washed with water and eluted with 20% aqueous ethanol. The eluate was concentrated under reduced pressure and then lyophilized to give 155 mg of the title compound as a pale yellow powder.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature for 4 hours
  3. washbeing eluted with aceton/water (95:5)
  4. concentrationThe eluate was concentrated to dryness under reduced pressure
  5. customto obtain a powder to which
  6. stirringAfter stirring at room temperature for 14 hours
  7. distillationthe mixture was distilled under reduced pressure
  8. customto remove formic acid
  9. additionThe residue was added with water and THF
  10. temperaturecooling
  11. washwashed with ethyl acetate
  12. concentrationconcentrated under reduced pressure
  13. washbeing washed with water
  14. washeluted with 20% aqueous ethanol
  15. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fcd83888aee3408e8ff31c147ac5347c
Source dataset
uspto-grants-1990_11
Patent number
US04971963

Reaction notes

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