Hydrochloric Acid → Amphotericin B

HRID 2372679Notes

Reaction equation

HRID 2372679 reaction equation
[ClH:1].[CH3:2][C@@H:3]1[C@@H:42]([OH:43])[C@@H:41]([CH3:44])[C@H:40]([CH3:45])[O:39][C:37](=[O:38])[CH2:36][C@H:35]([OH:46])[CH2:34][C@H:33]([OH:47])[CH2:32][CH2:31][C@@H:30]([OH:48])[C@H:29]([OH:49])[CH2:28][C@H:27]([OH:50])[CH2:26][C@@:24]2([OH:51])[O:25][C@H:20]([C@H:21]([C:53]([OH:55])=[O:54])[C@@H:22]([OH:52])[CH2:23]2)[CH2:19][C@@H:18]([O:56][C@@H:57]2[O:62][C@H:61]([CH3:63])[C@@H:60]([OH:64])[C@H:59]([NH2:65])[C@@H:58]2[OH:66])[CH:17]=[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]1>CO>[CH3:2][C@@H:3]1[C@@H:42]([OH:43])[C@@H:41]([CH3:44])[C@H:40]([CH3:45])[O:39][C:37](=[O:38])[CH2:36][C@H:35]([OH:46])[CH2:34][C@H:33]([OH:47])[CH2:32][CH2:31][C@@H:30]([OH:48])[C@H:29]([OH:49])[CH2:28][C@H:27]([OH:50])[CH2:26][C@@:24]2([OH:51])[O:25][C@H:20]([C@H:21]([C:53]([OH:55])=[O:54])[C@@H:22]([OH:52])[CH2:23]2)[CH2:19][C@@H:18]([O:56][C@@H:57]2[O:62][C@H:61]([CH3:63])[C@@H:60]([OH:64])[C@H:59]([NH2:65])[C@@H:58]2[OH:66])[CH:17]=[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]1.[ClH:1].[CH3:2][C@@H:3]1[C@@H:42]([OH:43])[C@@H:41]([CH3:44])[C@H:40]([CH3:45])[O:39][C:37](=[O:38])[CH2:36][C@H:35]([OH:46])[CH2:34][C@H:33]([OH:47])[CH2:32][CH2:31][C@@H:30]([OH:48])[C@H:29]([OH:49])[CH2:28][C@H:27]([OH:50])[CH2:26][C@@:24]2([OH:51])[O:25][C@H:20]([C@H:21]([C:53]([OH:55])=[O:54])[C@@H:22]([OH:52])[CH2:23]2)[CH2:19][C@@H:18]([O:56][C@@H:57]2[O:62][C@H:61]([CH3:63])[C@@H:60]([OH:64])[C@H:59]([NH2:65])[C@@H:58]2[OH:66])[CH:17]=[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]1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid3×HCID 5280965Amphotericin B4×

Product 2

HCID 5280965Amphotericin BHCID 86745589HCID 86745589, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In order to study the effect of adding HCl on the stability of amphotericin B, increasing amounts of amphotericin B (i.v. grade) were dissolved in methanol in the presence of one equivalent of HCl (methanolic solution). The degradation in an acid medium of the substance of amphotericin B increases greatly when the amphotericin B concentration is greater than 2 mg/ml (see FIG. 1), even when the addition of HCl in methanolic solution has been carried out at 0° C. (with a 31% contamination). To obtain an amphotericin B/HCl solution at a concentration of 5 mg/ml without degradation of the amphotericin B, amphotericin B was dissolved in methanol in the presence of one equivalent of HCl at a concentration of 2 mg/ml. The solvent was then evaporated off and the salt of amphotericin B with the acid was redissolved in the requisite volume of alcohol.

Workup

  1. customhas been carried out at 0° C.

Sources & evidence

ORD record
ord-026dc97e5e92473b8a2bc2aabe485f19
Source dataset
uspto-grants-1992_03
Patent number
US05100591

Reaction notes

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