Methanol → HCID 178441400, compound

HRID 2231430Notes

Reaction equation

HRID 2231430 reaction equation
[C:1](=O)([O-:3])[O-:2].[Ba+2].[CH3:6][CH2:7][CH2:8][CH2:9][CH:10]1[C:45](=[O:46])[O:44][CH:43]([CH:47]([CH:49]([OH:57])[CH2:50][CH2:51][CH2:52][NH:53][C:54]([NH2:56])=[NH:55])[CH3:48])[CH:42]([CH3:58])[CH:41]=[C:40]([CH3:59])[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]([OH:60])[CH2:34][CH:33]([OH:61])[CH2:32][CH:31]([OH:62])[CH2:30][CH:29]([OH:63])[CH2:28][CH:27]([OH:64])[CH:26]([O:65][C@H:66]2[O:70][C@H:69]([CH2:71][OH:72])[C@@H:68]([OH:73])[C@@H:67]2[OH:74])[CH:25]=[C:24]([CH3:75])[CH:23]([OH:76])[CH2:22][CH2:21][CH2:20][CH:19]([OH:77])[CH2:18][CH2:17][CH2:16][CH:15]([OH:78])[CH2:14][CH2:13][CH:12]([CH3:79])[CH:11]1[OH:80].S([O-])([O-])(=O)=O.CO>C(O)=O>[CH3:6][CH2:7][CH2:8][CH2:9][CH:10]1[C:45](=[O:46])[O:44][CH:43]([CH:47]([CH:49]([OH:57])[CH2:50][CH2:51][CH2:52][NH:53][C:54]([NH2:56])=[NH:55])[CH3:48])[CH:42]([CH3:58])[CH:41]=[C:40]([CH3:59])[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]([OH:60])[CH2:34][CH:33]([OH:61])[CH2:32][CH:31]([OH:62])[CH2:30][CH:29]([OH:63])[CH2:28][CH:27]([OH:64])[CH:26]([O:65][C@H:66]2[O:70][C@H:69]([CH2:71][OH:72])[C@@H:68]([OH:73])[C@@H:67]2[OH:74])[CH:25]=[C:24]([CH3:75])[CH:23]([OH:76])[CH2:22][CH2:21][CH2:20][CH:19]([OH:77])[CH2:18][CH2:17][CH2:16][CH:15]([OH:78])[CH2:14][CH2:13][CH:12]([CH3:79])[CH:11]1[OH:80].[CH:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 10563Barium CarbonateHCID 178441404HCID 178441404, compound

Product 1

HCID 178441400HCID 178441400, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

0.088 g (0.446 millimole) of barium carbonate are heated to boiling in 5 ml of formic acid until a clear solution is obtained. The colorless solution is evaporated to dryness in vacuo. The residue is dissolved in 10 ml of methanol and the solution thus obtained is added to a suspension of 1.0 g (0.887 millimole) or primycin sulfate and 70 ml of methanol. The reaction mixture is heated to boiling for 10 minutes under constant stirring. The precipitated barium sulfate is filtered hot through a Celite filtration auxiliary agent. The filtrate is evaporated in vacuo and the solid residue is treated with ether. The white powdery product is washed with 20 ml of a 2:1 mixture of acetone and water and thereafter with anhydrous ether. Thus 0.96 g of primycin formate is obtained, yield 94.8%. Mp.: 162°-164° C., /α/D25 =+31.9°. (in a 2:2:1 mixture of n-butanol, ethanol and water, c=0.1%)

Workup

  1. customis obtained
  2. customThe colorless solution is evaporated to dryness in vacuo
  3. dissolutionThe residue is dissolved in 10 ml of methanol
  4. customthe solution thus obtained
  5. temperatureThe reaction mixture is heated
  6. filtrationThe precipitated barium sulfate is filtered hot through a Celite filtration auxiliary agent
  7. customThe filtrate is evaporated in vacuo
  8. additionthe solid residue is treated with ether
  9. washThe white powdery product is washed with 20 ml of a 2:1 mixture of acetone and water

Sources & evidence

ORD record
ord-e550637a829f44ed88762b8082959faa
Source dataset
uspto-grants-1988_11
Patent number
US04782141

Reaction notes

Loading…