Citric Acid → HCID 86735086, compound

HRID 2072241Notes

Reaction equation

HRID 2072241 reaction equation
[CH3:1][C@@H:2]1[C@@H:41]([OH:42])[C@@H:40]([CH3:43])[C@H:39]([CH3:44])[O:38][C:36](=[O:37])[CH2:35][C@H:34]([OH:45])[CH2:33][C@H:32]([OH:46])[CH2:31][CH2:30][C@@H:29]([OH:47])[C@H:28]([OH:48])[CH2:27][C@H:26]([OH:49])[CH2:25][C@@:23]2([OH:50])[O:24][C@H:19]([C@H:20]([C:52]([OH:54])=[O:53])[C@@H:21]([OH:51])[CH2:22]2)[CH2:18][C@@H:17]([O:55][C@@H:56]2[O:61][C@H:60]([CH3:62])[C@@H:59]([OH:63])[C@H:58]([NH2:64])[C@@H:57]2[OH:65])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=[CH:3]1.[Cl-].[Cl-].[Ca+2:68].Cl.[C:70]([OH:82])(=[O:81])[CH2:71][C:72]([CH2:77][C:78]([OH:80])=[O:79])([C:74]([OH:76])=[O:75])[OH:73].[NH4+].[OH-]>CO.O>[CH3:1][C@@H:2]1[C@@H:41]([OH:42])[C@@H:40]([CH3:43])[C@H:39]([CH3:44])[O:38][C:36](=[O:37])[CH2:35][C@H:34]([OH:45])[CH2:33][C@H:32]([OH:46])[CH2:31][CH2:30][C@@H:29]([OH:47])[C@H:28]([OH:48])[CH2:27][C@H:26]([OH:49])[CH2:25][C@@:23]2([OH:50])[O:24][C@H:19]([C@H:20]([C:52]([OH:54])=[O:53])[C@@H:21]([OH:51])[CH2:22]2)[CH2:18][C@@H:17]([O:55][C@@H:56]2[O:61][C@H:60]([CH3:62])[C@@H:59]([OH:63])[C@H:58]([NH2:64])[C@@H:57]2[OH:65])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=[CH:3]1.[Ca:68].[C:70]([OH:82])(=[O:81])[CH2:71][C:72]([CH2:77][C:78]([OH:80])=[O:79])([C:74]([OH:76])=[O:75])[OH:73]

Participants

8

Reactant 5

HCID 311Citric AcidHCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 5280965Amphotericin BHCID 5284359Calcium Chloride

Product 1

HCID 86735086HCID 86735086, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

10.66 g of amphotericin B (938γ/mg of activity-equivalent to 10 g of chemical activity) suspended in 2.5 liters anhydrous methanol containing 11.1 ml of 5% CaCl2 in methanol (equivalent to 200 mg Ca ion) is solubilized by means of 1.75 ml of 5.8 N HCl (pH 3.9). To the resulting solution is added 10.9 g of reagent grade citric acid. H2O (equivalent to 10 g anhydrous citric acid) to form a mixture of pH 2. The pH of the mixture is adjusted to about 7 by the addition of 7.9 ml concentrated NH4OH. The mixture is then heated to 45°-50° C. and slurried for 1 hour and thereafter is cooled to room temperature, filtered and the wet cake dried overnight under vacuum at 45°-50° C. to yield 10 g of complex.

Workup

  1. additiona mixture of pH 2
  2. temperatureThe mixture is then heated to 45°-50° C.
  3. filtrationfiltered
  4. customthe wet cake dried overnight under vacuum at 45°-50° C.

Sources & evidence

ORD record
ord-123184c8d77b4521b8bf4631a7705db7
Source dataset
uspto-grants-1977_09
Patent number
US04049898

Reaction notes

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