Acetone → Amphoglucamine

HRID 1414857Notes

Reaction equation

HRID 1414857 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.[NH:66]([CH2:68][C@@H:69]([C@H:71]([C@@H:73]([C@@H:75]([CH2:77][OH:78])[OH:76])[OH:74])[OH:72])[OH:70])[CH3:67].CC(C)=O.C(OCC)C>CS(C)=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.[CH3:67][NH:66][CH2:68][C@H:69]([OH:70])[C@@H:71]([OH:72])[C@H:73]([OH:74])[C@H:75]([OH:76])[CH2:77][OH:78]

Participants

6

Reactant 4

HCID 180AcetoneHCID 3283Diethyl EtherHCID 8567N-Methyl-D-glucamine2×HCID 5280965Amphotericin B

Product 1

HCID 6449900AmphoglucamineYield 137%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

19.7 g of amphotericin B with a specific biological activity of 750 mcg/mg (ED/mg) and 14.7 g of meglumine with the content of 1-deoxy-1-(methylamino)-glucitol of at least 99% are dissolved in 100 ml of dimethylsulphoxide at a temperature within the range of from 50° to 60° C and stirred for 10 minutes. The resulting solution is added with a 7-fold volume of a mixture of acetone with diethyl ether (in a volumetric ratio of 1:1). The precipitate is filtered off, washed with the same mixture of acetone with diethyl ether, and dried at 20° C under a residual pressure of 100 mm Hg to give 32.7 g of amphoglucamine with a specific biological activity of 440 mcg/mg (ED/mg) which corresponds to the yield of 96% of amphoglucamine based on the activity of the starting amphotericin B.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with the same mixture of acetone with diethyl ether
  3. customdried at 20° C under a residual pressure of 100 mm Hg

Sources & evidence

ORD record
ord-c61b9266f8f449cf81e7bc21f8e7fae3
Source dataset
uspto-grants-1977_01
Patent number
US04002741

Reaction notes

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