Ethanol → Caspofungin Acetate

HRID 2173738

Reaction equation

HRID 2173738 reaction equation
[CH3:1][CH2:2][CH:3]([CH2:5][CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:18][C@@H:19]1[C:50](=[O:51])[NH:49][C@@H:48]([C@H:52]([OH:54])[CH3:53])[C:46](=[O:47])[N:45]2[C@@H:41]([CH2:42][C@@H:43]([OH:55])[CH2:44]2)[C:39](=[O:40])[NH:38][C@@H:37]([C@H:56]([OH:66])[C@@H:57]([OH:65])[C:58]2[CH:59]=[CH:60][C:61]([OH:64])=[CH:62][CH:63]=2)[C:35](=[O:36])[NH:34][C@@H:33]([C@H:67]([OH:71])[CH2:68][CH2:69][NH2:70])[C:31](=[O:32])[N:30]2[C@@H:26]([C@@H:27]([OH:72])[CH2:28][CH2:29]2)[C:24](=[O:25])[NH:23][C@H:22]([NH:73][CH2:74][CH2:75][NH2:76])[C@H:21]([OH:77])[CH2:20]1)=[O:17])[CH3:7])[CH3:4].C(O)C.[C:81]([O:84]CC)(=[O:83])[CH3:82].N[C@H:88]([C:97]([OH:99])=[O:98])CC1C=CC(O)=CC=1>CO[2H].C(O)(=O)C>[CH3:1][CH2:2][CH:3]([CH2:5][CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:18][C@@H:19]1[C:50](=[O:51])[NH:49][C@@H:48]([C@H:52]([OH:54])[CH3:53])[C:46](=[O:47])[N:45]2[C@@H:41]([CH2:42][C@@H:43]([OH:55])[CH2:44]2)[C:39](=[O:40])[NH:38][C@@H:37]([C@H:56]([OH:66])[C@@H:57]([OH:65])[C:58]2[CH:59]=[CH:60][C:61]([OH:64])=[CH:62][CH:63]=2)[C:35](=[O:36])[NH:34][C@@H:33]([C@H:67]([OH:71])[CH2:68][CH2:69][NH2:70])[C:31](=[O:32])[N:30]2[C@@H:26]([C@@H:27]([OH:72])[CH2:28][CH2:29]2)[C:24](=[O:25])[NH:23][C@H:22]([NH:73][CH2:74][CH2:75][NH2:76])[C@H:21]([OH:77])[CH2:20]1)=[O:17])[CH3:7])[CH3:4].[CH3:82][C:81]([OH:84])=[O:83].[CH3:88][C:97]([OH:99])=[O:98]

Participants

7

Reactant 4

HCID 702EthanolHCID 6057L-TyrosineHCID 8857Ethyl AcetateHCID 2826718n-{(2r,6s,9s,11r,12s,14As,15s,20s,23s,25as)-12-[(2-aminoethyl)amino]-20-[(1r)-3-amino-1-hydroxypropyl]-23-[(1s,2s)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,15-trihydroxy-6-[(1r)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxotetracosahydro-1h-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl}-10,12-dimethyltetradecanamide2×

Product 1

HCID 6850808Caspofungin Acetate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 123113Methan(2H)olSolvent

Procedure

By means of NMR the contents of caspofungin, ethanol, ethyl acetate and acetic acid were determined in the crystals obtained above as follows. Approximately 15 mg of sample and standard (DMB) were accurately weighed in a suitable vial. The samples were dissolved in MeOD by vortexing. The samples were measured at 600 MHz using a delay of 30 s at 300K. The spectra that were used for the calculation of the impurities in the aromatic region were measured using a delay of 5 s and 256 scans to enhance the signal to noise ratio. The analysis was carried out in duplo. Caspofungin was quantified using the tyrosine signal at 7.15 ppm. See Table 5 for results.

Workup

  1. customobtained above
  2. customfor results

Sources & evidence

ORD record
ord-e39fd8ca65ae4faeabc33b9378de8bba
Source dataset
uspto-grants-2015_06
Patent number
US09056897B2

Linked notes

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