1-Butanol → N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-Dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]hexadecanamide

HRID 1284288Notes

Reaction equation

HRID 1284288 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:18][CH:19]1[C:50](=[O:51])[NH:49][CH:48]([CH:52]([OH:54])[CH3:53])[C:46](=[O:47])[N:45]2[CH:41]([CH2:42][CH:43]([OH:55])[CH2:44]2)[C:39](=[O:40])[NH:38][CH:37]([CH:56]([OH:66])[CH:57]([OH:65])[C:58]2[CH:63]=[CH:62][C:61]([OH:64])=[CH:60][CH:59]=2)[C:35](=[O:36])[NH:34][CH:33]([CH:67]([OH:69])[CH3:68])[C:31](=[O:32])[N:30]2[CH:26]([CH:27]([OH:71])[CH:28]([CH3:70])[CH2:29]2)[C:24](=[O:25])[NH:23][CH:22]([OH:72])[CH:21]([OH:73])[CH2:20]1)=[O:17].C(O)CCC.O>C(OCC)(=O)C.C(O)CCC>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:18][C@@H:19]1[C:50](=[O:51])[NH:49][C@@H:48]([C@H:52]([OH:54])[CH3:53])[C:46](=[O:47])[N:45]2[C@@H:41]([CH2:42][C@@H:43]([OH:55])[CH2:44]2)[C:39](=[O:40])[NH:38][C@@H:37]([C@H:56]([OH:66])[C@@H:57]([OH:65])[C:58]2[CH:59]=[CH:60][C:61]([OH:64])=[CH:62][CH:63]=2)[C:35](=[O:36])[NH:34][C@@H:33]([C@H:67]([OH:69])[CH3:68])[C:31](=[O:32])[N:30]2[C@@H:26]([C@@H:27]([OH:71])[C@@H:28]([CH3:70])[CH2:29]2)[C:24](=[O:25])[NH:23][C@H:22]([OH:72])[C@H:21]([OH:73])[CH2:20]1)=[O:17]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 962WaterHCID 122233Aculeacin A from aspergillus aculeatus

Product 1

HCID 14315169N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-Dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]hexadecanamide

Reagents, catalysts & solvents 1

HCID 22004815Ethyl acetate n-butanolSolvent

Procedure

1.7 g. of crude aculeacins obtained in Example 2 dissolved in 5 ml. of n-butanol was charged on a silica gel column packed with a water-saturated solvent of ethyl acetate-n-butanol (4 : 1). The column was eluted with the same solvent and 10 g. fractions were collected. Each fraction was assayed by bio-assay and thin layer chromatograph to find the activity of Nos. 33 to 55 fractions. Vacuum drying gave 629 mg. of white powder. The powder was further purified by dissolving in n-butanol (50 ml.), and was washed three times with distilled water (each 10 ml.) and dried in vacuo. 577 mg. of purified aculeacin-A was obtained.

Workup

  1. washThe column was eluted with the same solvent and 10 g
  2. customfractions were collected
  3. customVacuum drying
  4. customgave 629 mg
  5. customThe powder was further purified
  6. dissolutionby dissolving in n-butanol (50 ml.)
  7. washwas washed three times with distilled water (each 10 ml
  8. custom) and dried in vacuo

Sources & evidence

ORD record
ord-39ba9758d4674c1099f958462723bc60
Source dataset
uspto-grants-1976_08
Patent number
US03978210

Reaction notes

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