Hydrochloric Acid → HCID 131724508, compound

HRID 1835000Notes

Reaction equation

HRID 1835000 reaction equation
Cl.[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.[CH3:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][C:84]([O:86][CH2:87][CH:88]([O:100][C:101]([CH2:103][CH2:104][CH2:105][CH2:106][CH2:107][CH2:108][CH2:109][CH2:110][CH2:111][CH2:112][CH2:113][CH2:114][CH2:115][CH2:116][CH2:117][CH2:118][CH3:119])=[O:102])[CH2:89][O:90][P:91]([O:94][CH2:95][CH:96]([OH:99])[CH2:97][OH:98])([OH:93])=[O:92])=[O:85]>C(Cl)(Cl)Cl.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.[CH3:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][C:84]([O:86][CH2:87][CH:88]([O:100][C:101]([CH2:103][CH2:104][CH2:105][CH2:106][CH2:107][CH2:108][CH2:109][CH2:110][CH2:111][CH2:112][CH2:113][CH2:114][CH2:115][CH2:116][CH2:117][CH2:118][CH3:119])=[O:102])[CH2:89][O:90][P:91]([O:94][CH2:95][CH:96]([OH:99])[CH2:97][OH:98])([OH:93])=[O:92])=[O:85]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 651453-{[(2,3-Dihydroxypropoxy)(hydroxy)phosphoryl]oxy}-2-(octadecanoyloxy)propyl octadecanoateHCID 5280965Amphotericin B

Product 1

HCID 131724508HCID 131724508, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent2×

Procedure

632.7 mg distearoylphosphatidylglycerol sodium salt (Avanti Polar Lipids, Birmingham, Ala.) was dissolved in 4 ml of an equivolume solution of chloroform and methanol at 65° Centigrade. 300 ul 2.5 M HCl was added to the solution. 375.9 mg Amphotericin B (Squibb Pharmaceuticals, New Brunswick, N.J.) was first suspended in 4.0 ml of equivolume solution of chloroform and methanol, and then the suspension was added to the acidified DSPG solution. The Amphotericin B—DSPG lipophilic complex was formed with heating at 65° C. for several minutes yielding an orange solution of the dissolved Amphotericin B complex with a pH of approximately 1.5. The concentration of Amphotericin B was approximately 45 mg/ml.

Sources & evidence

ORD record
ord-4fd5c44087ba48fa82eff4e664a7ce6b
Source dataset
uspto-grants-2004_08
Patent number
US06770290B1

Reaction notes

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