HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylenediamine | HCID 3301 | — |
| Reactant | Thiophenol | HCID 7969 | — |
| Reactant | (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 | HCID 5742645 | — |
| Product | 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 | HCID 2826718 | — |
Reaction Steps
According to WO96/24613 and U.S. Pat. No. 5,552,521, 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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08912309B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-7744568466c549a6821ff71f8c1b6265 |
| Source note | uspto-grants-2014_12 |