Trifluoroacetic acid → HCID 20779519, compound

HRID 2180875Notes

Reaction equation

HRID 2180875 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][CH2:16][C@@H:17]([C:32]([NH:34][C:35]1[CH:40]=[CH:39][C:38]([CH:41]([C:75]2[CH:80]=[CH:79][C:78]([NH:81][C:82](=[O:107])[C@H:83]([CH2:98][CH2:99][C:100]([O:102]C(C)(C)C)=[O:101])[NH:84][C:85](=[O:97])[CH2:86][C:87]3[C:95]4[C:90](=[CH:91][CH:92]=[CH:93][CH:94]=4)[NH:89][C:88]=3[CH3:96])=[CH:77][CH:76]=2)[C:42]2[CH:47]=[CH:46][C:45]([NH:48][C:49](=[O:74])[C@H:50]([CH2:65][CH2:66][C:67]([O:69]C(C)(C)C)=[O:68])[NH:51][C:52](=[O:64])[CH2:53][C:54]3[C:62]4[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=4)[NH:56][C:55]=3[CH3:63])=[CH:44][CH:43]=2)=[CH:37][CH:36]=1)=[O:33])[NH:18][C:19](=[O:31])[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][C:22]=1[CH3:30])=[O:14])(C)(C)C>CO>[CH3:96][C:88]1[NH:89][C:90]2[C:95]([C:87]=1[CH2:86][C:85]([NH:84][C@H:83]([C:82]([NH:81][C:78]1[CH:77]=[CH:76][C:75]([CH:41]([C:38]3[CH:37]=[CH:36][C:35]([NH:34][C:32](=[O:33])[C@H:17]([CH2:16][CH2:15][C:13](=[O:12])[OH:14])[NH:18][C:19](=[O:31])[CH2:20][C:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[NH:23][C:22]=4[CH3:30])=[CH:40][CH:39]=3)[C:42]3[CH:47]=[CH:46][C:45]([NH:48][C:49](=[O:74])[C@H:50]([CH2:65][CH2:66][C:67](=[O:68])[OH:69])[NH:51][C:52](=[O:64])[CH2:53][C:54]4[C:62]5[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=5)[NH:56][C:55]=4[CH3:63])=[CH:44][CH:43]=3)=[CH:80][CH:79]=1)=[O:107])[CH2:98][CH2:99][C:100](=[O:101])[OH:102])=[O:97])=[CH:94][CH:93]=[CH:92][CH:91]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20779510HCID 20779510, compound

Product 1

HCID 20779519HCID 20779519, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A methanol solution containing trifluoroacetic acid (40%, 6 ml) was added to the tris[4-[β-t-butoxycarbonylmethyl-N-[2-(2-methyl-1H-indol-3-yl)acetyl]-L-alanyl]aminophenyl]methane (50 mg) at room temperature, and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, a portion of the residue was purified by preparative high performance liquid chromatography using methanol/trifluoroacetic acid (100/0.1) and water/trifluoroacetic acid (100/0.1) as a mixed eluent, to obtain 2.0 mg of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customa portion of the residue was purified by preparative high performance liquid chromatography

Sources & evidence

ORD record
ord-25843aedc94c4a1790a9d92b3421dab2
Source dataset
uspto-grants-2005_05
Patent number
US06887890B2

Reaction notes

Loading…