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 870306

Reaction equation

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]

Participants

Reactant 4

HCID 3301Ethylenediamine

HCID 127654-Methoxybenzenethiol

HCID 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

Product 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

Procedure

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 3 A molecular sieve, and then the resulting product reacts with ethylenediamine to obtain caspofungin.

Sources & evidence

ORD record: ord-f649d0f5461c49ffb4f491dcc14df1a5
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969513B2

Linked notes

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