Oxalic Acid → HCID 178441403, compound

HRID 2231434Notes

Reaction equation

HRID 2231434 reaction equation
C(=O)([O-])[O-].[Ba+2].[C:6]([OH:11])(=[O:10])[C:7]([OH:9])=[O:8].[CH3:12][CH2:13][CH2:14][CH2:15][CH:16]1[C:51](=[O:52])[O:50][CH:49]([CH:53]([CH:55]([OH:63])[CH2:56][CH2:57][CH2:58][NH:59][C:60]([NH2:62])=[NH:61])[CH3:54])[CH:48]([CH3:64])[CH:47]=[C:46]([CH3:65])[CH2:45][CH2:44][CH2:43][CH2:42][CH:41]([OH:66])[CH2:40][CH:39]([OH:67])[CH2:38][CH:37]([OH:68])[CH2:36][CH:35]([OH:69])[CH2:34][CH:33]([OH:70])[CH:32]([O:71][C@H:72]2[O:76][C@H:75]([CH2:77][OH:78])[C@@H:74]([OH:79])[C@@H:73]2[OH:80])[CH:31]=[C:30]([CH3:81])[CH:29]([OH:82])[CH2:28][CH2:27][CH2:26][CH:25]([OH:83])[CH2:24][CH2:23][CH2:22][CH:21]([OH:84])[CH2:20][CH2:19][CH:18]([CH3:85])[CH:17]1[OH:86].S([O-])([O-])(=O)=O>CO>[CH3:12][CH2:13][CH2:14][CH2:15][CH:16]1[C:51](=[O:52])[O:50][CH:49]([CH:53]([CH:55]([OH:63])[CH2:56][CH2:57][CH2:58][NH:59][C:60]([NH2:62])=[NH:61])[CH3:54])[CH:48]([CH3:64])[CH:47]=[C:46]([CH3:65])[CH2:45][CH2:44][CH2:43][CH2:42][CH:41]([OH:66])[CH2:40][CH:39]([OH:67])[CH2:38][CH:37]([OH:68])[CH2:36][CH:35]([OH:69])[CH2:34][CH:33]([OH:70])[CH:32]([O:71][C@H:72]2[O:76][C@H:75]([CH2:77][OH:78])[C@@H:74]([OH:79])[C@@H:73]2[OH:80])[CH:31]=[C:30]([CH3:81])[CH:29]([OH:82])[CH2:28][CH2:27][CH2:26][CH:25]([OH:83])[CH2:24][CH2:23][CH2:22][CH:21]([OH:84])[CH2:20][CH2:19][CH:18]([CH3:85])[CH:17]1[OH:86].[C:6]([O-:11])(=[O:10])[C:7]([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 10563Barium CarbonateHCID 178441404HCID 178441404, compound

Product 1

HCID 178441403HCID 178441403, compoundYield 179.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.087 g (0.444 millimoles) of barium carbonate are suspended in 15 ml of mthanol whereupon 0.04 g (0.444 millimoles) of oxalic acid are added. The suspension thus obtained is heated to boiling until all the solid is dissolved (about 10 minutes). The solvent is removed in vacuo. The residue is added to a solution of 1.0 g (0.887 millimoles) of primycin sulfate and 80 ml of methanol and the reaction mixture is heated to boiling for 20 minutes under constant stirring. The precipitated barium sulfate is filtered hot over Celite. The filtrate is evaporated in vacuo. The solid residue is treated with ether and filtered. The solid is washed on the filter with a 2:1 mixture of acetone and water. Thus 0.93 g of white primycin oxalate is obtained, yield 92.2%. Mp.: 186°-187° C., /α/D25 =+40°.

Workup

  1. additionare added
  2. customThe suspension thus obtained
  3. temperatureis heated
  4. dissolutionis dissolved (about 10 minutes)
  5. customThe solvent is removed in vacuo
  6. temperaturethe reaction mixture is heated
  7. filtrationThe precipitated barium sulfate is filtered hot over Celite
  8. customThe filtrate is evaporated in vacuo
  9. additionThe solid residue is treated with ether
  10. filtrationfiltered
  11. washThe solid is washed on the
  12. filtrationfilter with a 2:1 mixture of acetone and water

Sources & evidence

ORD record
ord-8a943763963d446bb305abcf60f45e8d
Source dataset
uspto-grants-1988_11
Patent number
US04782141

Reaction notes

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