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 874910

Reaktionsgleichung

Reaktionsgleichung von HRID 874910
COC1C=CC(S)=CC=1.B([O-])([O-])OC1C=CC=CC=1.[CH2:20]([NH2:23])[CH2:21][NH2:22].[CH3:24][CH2:25][CH:26]([CH2:28][CH:29]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([NH:41][C@@H:42]1[C:73](=[O:74])[NH:72][C@@H:71]([C@H:75]([OH:77])[CH3:76])[C:69](=[O:70])[N:68]2[C@@H:64]([CH2:65][C@@H:66]([OH:78])[CH2:67]2)[C:62](=[O:63])[NH:61][C@@H:60]([C@H:79]([OH:89])[C@@H:80]([OH:88])[C:81]2[CH:86]=[CH:85][C:84]([OH:87])=[CH:83][CH:82]=2)[C:58](=[O:59])[NH:57][C@@H:56]([C@H:90]([OH:95])[CH2:91][C:92]([NH2:94])=O)[C:54](=[O:55])[N:53]2[C@@H:49]([C@@H:50]([OH:96])[CH2:51][CH2:52]2)[C:47](=[O:48])[NH:46][C@H:45](O)[C@H:44]([OH:98])[CH2:43]1)=[O:40])[CH3:30])[CH3:27]>>[CH3:24][CH2:25][CH:26]([CH2:28][CH:29]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([NH:41][C@@H:42]1[C:73](=[O:74])[NH:72][C@@H:71]([C@H:75]([OH:77])[CH3:76])[C:69](=[O:70])[N:68]2[C@@H:64]([CH2:65][C@@H:66]([OH:78])[CH2:67]2)[C:62](=[O:63])[NH:61][C@@H:60]([C@H:79]([OH:89])[C@@H:80]([OH:88])[C:81]2[CH:86]=[CH:85][C:84]([OH:87])=[CH:83][CH:82]=2)[C:58](=[O:59])[NH:57][C@@H:56]([C@H:90]([OH:95])[CH2:91][CH2:92][NH2:94])[C:54](=[O:55])[N:53]2[C@@H:49]([C@@H:50]([OH:96])[CH2:51][CH2:52]2)[C:47](=[O:48])[NH:46][C@H:45]([NH:22][CH2:21][CH2:20][NH2:23])[C@H:44]([OH:98])[CH2:43]1)=[O:40])[CH3:30])[CH3:27]

Komponenten

5

Edukt 4

HCID 3301EthylenediamineHCID 127654-MethoxybenzenethiolHCID 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-hexaone2×HCID 19793864Phenylborate

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 WO2010008493A2, Pneumocandin B0 as the starting material reacts with 4-methoxy thiophenol, the resulting product is protected by phenyl borate, the amide group in Pneumocandin B0 is reduced to amine group under the condition of dehydration by 3A molecular sieve, and then the resulting product reacts with ethylenediamine to obtain caspofungin.

Quellen und Nachweise

ORD-Eintrag
ord-ee57692286c0421785c82e38b6a0e61b
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981048B2

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