Ethylenediamine → n-{(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-dimethyltetradecanamide

HRID 870304

Reaktionsgleichung

Reaktionsgleichung von HRID 870304
C1(S)C=CC=CC=1.[CH2:8]([NH2:11])[CH2:9][NH2:10].[CH3:12][CH2:13][CH:14]([CH2:16][CH:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([NH:29][C@@H:30]1[C:61](=[O:62])[NH:60][C@@H:59]([C@H:63]([OH:65])[CH3:64])[C:57](=[O:58])[N:56]2[C@@H:52]([CH2:53][C@@H:54]([OH:66])[CH2:55]2)[C:50](=[O:51])[NH:49][C@@H:48]([C@H:67]([OH:77])[C@@H:68]([OH:76])[C:69]2[CH:74]=[CH:73][C:72]([OH:75])=[CH:71][CH:70]=2)[C:46](=[O:47])[NH:45][C@@H:44]([C@H:78]([OH:83])[CH2:79][C:80]([NH2:82])=O)[C:42](=[O:43])[N:41]2[C@@H:37]([C@@H:38]([OH:84])[CH2:39][CH2:40]2)[C:35](=[O:36])[NH:34][C@H:33](O)[C@H:32]([OH:86])[CH2:31]1)=[O:28])[CH3:18])[CH3:15]>>[CH3:12][CH2:13][CH:14]([CH2:16][CH:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([NH:29][C@@H:30]1[C:61](=[O:62])[NH:60][C@@H:59]([C@H:63]([OH:65])[CH3:64])[C:57](=[O:58])[N:56]2[C@@H:52]([CH2:53][C@@H:54]([OH:66])[CH2:55]2)[C:50](=[O:51])[NH:49][C@@H:48]([C@H:67]([OH:77])[C@@H:68]([OH:76])[C:69]2[CH:74]=[CH:73][C:72]([OH:75])=[CH:71][CH:70]=2)[C:46](=[O:47])[NH:45][C@@H:44]([C@H:78]([OH:83])[CH2:79][CH2:80][NH2:82])[C:42](=[O:43])[N:41]2[C@@H:37]([C@@H:38]([OH:84])[CH2:39][CH2:40]2)[C:35](=[O:36])[NH:34][C@H:33]([NH:10][CH2:9][CH2:8][NH2:11])[C@H:32]([OH:86])[CH2:31]1)=[O:28])[CH3:18])[CH3:15]

Komponenten

4

Edukt 3

HCID 3301EthylenediamineHCID 7969ThiophenolHCID 5742645(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-(2-Carbamoyl-1(R)-hydroxyethyl)-23-(1(S),2(S)-dihydroxy-2-(4-hydroxyphenyl)ethyl)-9-(10,12-dimethyltetradecanamido)-2,11,12,15-tetrahydroxy-6-(1(R)-hydroxyethyl)perhydrodipyrrolo(2,1-c:2',1'-l)(1,4,7,10,13,16)hexaazacycloheneicosine-5,8,14,19,22,25-hexaone

Produkt 1

HCID 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-dimethyltetradecanamide

Versuchsvorschrift

According to WO96/24613 and US5552521, the primary amide group in Pneumocandin B0 is reduced to amine group (47% of yield), and then the resulting product reacts with thiophenol and ethylenediamine in turn to obtain caspofungin.

Quellen und Nachweise

ORD-Eintrag
ord-4d5665f18d3e47d0b70e834f6b8eb5f6
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969513B2

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