Phosphoric Acid → HCID 131712060, compound

HRID 1660632Notes

Reaction equation

HRID 1660632 reaction equation
[C:1]([NH:11][C@@H:12]1[C:24](=[O:25])[N:14]2[C:15]([C:21]([O-:23])=[O:22])=[C:16]([CH2:19][OH:20])[CH2:17][S:18][C@H:13]12)(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[Na+].OP(O)(O)=O>CN(C)C=O>[C:1]([NH:11][C@@H:12]1[C:24](=[O:25])[N:14]2[C:15]([C:21]([OH:23])=[O:22])=[C:16]([CH2:19][O:20][C:1](=[O:10])[CH:2]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[OH:3])[CH2:17][S:18][C@H:13]12)(=[O:10])[CH:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[OH:3]

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 131712061HCID 131712061, compound

Product 1

HCID 131712060HCID 131712060, compoundYield 147.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (40 ml) was dissolved sodium 7β-mandelamido-3-hydroxymethyl-3-cephem-4-carboxylate (3.86 g), followed by addition of O-carboxymandelic anhydride (2.67 g). The mixture was stirred at room temperature for 30 minutes, after which 2% H3PO4 (150 ml) was added. The mixture was extracted with ethyl acetate (250 ml) and the ethyl acetate layer was rinsed with water (150 ml×2), dried (over magnesium sulfate) and concentrated under reduced pressure. Then, upon addition of ether, there was obtained a powder. This powder was recovered by filtration, washed with ether and dried under reduced pressure over phosphorus pentoxide. The procedure provided 7β-mandelamido-3-mandelyloxymethyl-3-cephem-4-carboxylic acid (3.68 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (250 ml)
  2. washthe ethyl acetate layer was rinsed with water (150 ml×2)
  3. dry with materialdried (over magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. additionThen, upon addition of ether
  6. customthere was obtained a powder
  7. filtrationThis powder was recovered by filtration
  8. washwashed with ether
  9. dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record
ord-affc665a8b1f470d8a1db669b138d743
Source dataset
uspto-grants-1981_12
Patent number
US04308381

Reaction notes

Loading…