HCID 178453385, compound → beta-Amanitin hexamethylenediamide

HRID 589425Notes

Reaction equation

HRID 589425 reaction equation
[CH3:1][CH2:2][CH:3]([CH:5]1[NH:27][C:25](=[O:26])[CH2:24][NH:23][C:21](=[O:22])[CH:20]2[NH:28][C:29]([CH:31]([CH:51]([CH:53]([OH:56])[CH2:54][OH:55])[CH3:52])[NH:32][C:33]([CH:35]3[N:39]([C:40]([CH:42]([CH2:46][C:47]([OH:49])=[O:48])[NH:43][C:44](=[O:45])[CH:13]([CH2:14][S:15]([C:17]4[NH:59][C:58]5[CH:60]=[C:61]([OH:64])[CH:62]=[CH:63][C:57]=5[C:18]=4[CH2:19]2)=[O:16])[NH:12][C:10](=[O:11])[CH2:9][NH:8][C:6]1=[O:7])=[O:41])[CH2:38][CH:37]([OH:50])[CH2:36]3)=[O:34])=[O:30])[CH3:4].C(OC([N-:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][NH-:79])=O)(C)(C)C>FC(F)(F)C(O)=O>[CH3:1][CH2:2][CH:3]([CH:5]1[NH:27][C:25](=[O:26])[CH2:24][NH:23][C:21](=[O:22])[CH:20]2[NH:28][C:29]([CH:31]([CH:51]([CH:53]([OH:56])[CH2:54][OH:55])[CH3:52])[NH:32][C:33]([CH:35]3[N:39]([C:40]([CH:42]([CH2:46][C:47]([OH:49])=[O:48])[NH:43][C:44](=[O:45])[CH:13]([CH2:14][S:15]([C:17]4[NH:59][C:58]5[CH:60]=[C:61]([OH:64])[CH:62]=[CH:63][C:57]=5[C:18]=4[CH2:19]2)=[O:16])[NH:12][C:10](=[O:11])[CH2:9][NH:8][C:6]1=[O:7])=[O:41])[CH2:38][CH:37]([OH:50])[CH2:36]3)=[O:34])=[O:30])[CH3:4].[NH-:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][NH-:79]

Participants

3

Reactant 1

HCID 178453385HCID 178453385, compound

Product 1

HCID 131734463beta-Amanitin hexamethylenediamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4.54 mg (4.05 μmol) β-Amanitin-(t-butyloxy-carbonyl)-hexamethylenediamide (I) was stirred at room temperature in 250 μl trifluoroacetic acid. After 2 minutes the excess TFA was evaporated at 20° C. and the remaining solid coevaporated 2 times with 1 ml acetonitrile and methanol. The crude amine was dissolved in 1000 μl dmso and prified on a LaPrep-HPLC: column: Kromasil 100-C18, 10 μm, 250×20 mm, with methanol/water (0.05% TFA), flow: 26 ml/min, detection at λ295 nm. Solvent A: 95% water: 5% methanol 0.05% trifluoroacetic acid. Solvent B: 10% water: 90% methanol 0.05% trifluoroacetic acid. Gradient: 0-5 min 100% A; 5-20 25 min 0% A; 25-27 min 100% A; 27-35 min 100% A. The fractions with the same retention time were collected and the solvents evaporated.

Workup

  1. customAfter 2 minutes the excess TFA was evaporated at 20° C.
  2. dissolutionThe crude amine was dissolved in 1000 μl dmso
  3. custom0-5 min 100% A
  4. custom5-20 25 min 0% A
  5. custom25-27 min 100% A
  6. custom27-35 min 100% A
  7. customThe fractions with the same retention time were collected
  8. customthe solvents evaporated

Sources & evidence

ORD record
ord-e56c075962344b6784d7c85b76c6bc3c
Source dataset
uspto-grants-2016_01
Patent number
US09233173B2

Reaction notes

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