Trifluoroacetic acid → HCID 131736693, compound

HRID 1482256Notes

Reaction equation

HRID 1482256 reaction equation
[NH2:1][C:2](=[O:100])[CH2:3][NH:4][C:5](=[O:99])[C@@H:6]([NH:13][C:14](=[O:98])[C@@H:15]([N:17]([CH3:97])[C:18]([C@H:20]([CH2:86][C:87](=[O:96])[S:88][CH2:89][C:90]1[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=1)[NH:21][C:22](=[O:85])[C@H:23]([CH2:78][C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1)[NH:24][C:25](=[O:77])[C@H:26]([CH:74]([CH3:76])[CH3:75])[NH:27][C:28](=[O:73])[C@H:29]([CH3:72])[NH:30][C:31](=[O:71])[C@H:32]([CH2:67][CH:68]([CH3:70])[CH3:69])[N:33]([CH3:66])[C:34](=[O:65])[CH2:35][NH:36][C:37](=[O:64])[C@H:38]([CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[N:39]([CH3:56])[C:40](=[O:55])[C@H:41]([CH3:54])[NH:42][C:43](=[O:53])[CH2:44][NH:45]C(=O)OC(C)(C)C)=[O:19])[CH3:16])[CH2:7][O:8]C(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:45][CH2:44][C:43](=[O:53])[NH:42][C@@H:41]([CH3:54])[C:40](=[O:55])[N:39]([CH3:56])[C@@H:38]([CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:37](=[O:64])[NH:36][CH2:35][C:34](=[O:65])[N:33]([CH3:66])[C@@H:32]([CH2:67][CH:68]([CH3:70])[CH3:69])[C:31](=[O:71])[NH:30][C@@H:29]([CH3:72])[C:28](=[O:73])[NH:27][C@@H:26]([CH:74]([CH3:75])[CH3:76])[C:25](=[O:77])[NH:24][C@@H:23]([CH2:78][C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1)[C:22](=[O:85])[NH:21][C@H:20]([C:18](=[O:19])[N:17]([C@@H:15]([CH3:16])[C:14]([NH:13][C@@H:6]([CH2:7][OH:8])[C:5]([NH:4][CH2:3][C:2]([NH2:1])=[O:100])=[O:99])=[O:98])[CH3:97])[CH2:86][C:87](=[O:96])[S:88][CH2:89][C:90]1[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736692HCID 131736692, compound

Product 1

HCID 131736693HCID 131736693, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

S-Benzyl (9S,12S,18S,21S,24S,27S,30S)-30-(((S)-1-(((S)-1-((2-amino-2-oxoethyl)amino)-3-(tert-butoxy)-1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)(methyl)carbamoyl)-12,27-dibenzyl-18-isobutyl-24-isopropyl-2,2,9,11,17,21-hexamethyl-4,7,10,13,16,19,22,25,28-nonaoxo-3-oxa-5,8,11,14,17,20,23,26,29-nonaazadotriacontane-32-thioate (Compound P-146) (11.8 mg, 0.0083 mmol) was dissolved in dichloromethane (150 μL), TFA (75.0 μL, 0.973 mmol) was added and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (0.1% aqueous FA solution: 0.1% FA-acetonitrile solution) to afford the title compound (7.3 mg, 69.5%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by column chromatography (0.1% aqueous FA solution: 0.1% FA-acetonitrile solution)

Sources & evidence

ORD record
ord-1e5b97d8487d43cdb2051b91adeb7bc9
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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