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 874910Notes

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

Sources & evidence

ORD record: ord-ee57692286c0421785c82e38b6a0e61b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08981048B2

Reaction notes

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