Trifluoroacetic acid → HCID 117736012, compound

HRID 1482271Notes

Reaction equation

HRID 1482271 reaction equation
FC(F)(F)C(O)=O.C([SiH](C(C)C)C(C)C)(C)C.[CH2:18]([C@@H:25]([C:83](=[O:158])[NH:84][CH2:85][C:86](=[O:157])[N:87]([CH3:156])[C@@H:88]([CH2:152][CH:153]([CH3:155])[CH3:154])[C:89](=[O:151])[N:90]([CH3:150])[C@@H:91]([CH:147]([CH3:149])[CH3:148])[C:92](=[O:146])[NH:93][C@@H:94]([CH2:139][C:140]1[CH:145]=[CH:144][CH:143]=[CH:142][CH:141]=1)[C:95](=[O:138])[NH:96][C@H:97]([C:113](=[O:137])[N:114]([CH3:136])[C@@H:115]([CH2:129][C:130]1[CH:135]=[CH:134][CH:133]=[CH:132][CH:131]=1)[C:116](=[O:128])[NH:117][C@@H:118]([CH3:127])[C:119](=[O:126])[N:120]1[CH2:125][CH2:124][CH2:123][CH2:122][CH2:121]1)[CH2:98][C:99]([O:101][C:102]1[C:107]([CH3:108])=[CH:106][CH:105]=[CH:104][C:103]=1[S:109][S:110][CH2:111][CH3:112])=[O:100])[N:26]([CH3:82])[C:27](=[O:81])[C@H:28]([C@H:59]([O:61]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:60])[NH:29][C:30](=[O:58])[C@H:31]([CH2:54][CH:55]([CH3:57])[CH3:56])[N:32]([CH3:53])[C:33](=[O:52])[C@H:34]([CH:49]([CH3:51])[CH3:50])[NH:35][C:36](=[O:48])[C@H:37]([CH3:47])[N:38](C)[C:39](=O)OC(C)(C)C)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[CH2:18]([C@@H:25]([C:83](=[O:158])[NH:84][CH2:85][C:86](=[O:157])[N:87]([CH3:156])[C@@H:88]([CH2:152][CH:153]([CH3:155])[CH3:154])[C:89](=[O:151])[N:90]([CH3:150])[C@@H:91]([CH:147]([CH3:149])[CH3:148])[C:92](=[O:146])[NH:93][C@@H:94]([CH2:139][C:140]1[CH:145]=[CH:144][CH:143]=[CH:142][CH:141]=1)[C:95](=[O:138])[NH:96][C@H:97]([C:113](=[O:137])[N:114]([CH3:136])[C@@H:115]([CH2:129][C:130]1[CH:131]=[CH:132][CH:133]=[CH:134][CH:135]=1)[C:116](=[O:128])[NH:117][C@@H:118]([CH3:127])[C:119](=[O:126])[N:120]1[CH2:125][CH2:124][CH2:123][CH2:122][CH2:121]1)[CH2:98][C:99]([O:101][C:102]1[C:107]([CH3:108])=[CH:106][CH:105]=[CH:104][C:103]=1[S:109][S:110][CH2:111][CH3:112])=[O:100])[N:26]([CH3:82])[C:27](=[O:81])[C@H:28]([C@H:59]([OH:61])[CH3:60])[NH:29][C:30](=[O:58])[C@H:31]([CH2:54][CH:55]([CH3:57])[CH3:56])[N:32]([CH3:53])[C:33](=[O:52])[C@H:34]([CH:49]([CH3:50])[CH3:51])[NH:35][C:36](=[O:48])[C@H:37]([CH3:47])[NH:38][CH3:39])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 131736697HCID 131736697, compound

Product 1

HCID 117736012HCID 117736012, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (100 ul) and triisopropylsilane (22.3 ul, 0.109 mmol) were added to a solution of 2-(ethyldisulfanyl)-6-methylphenyl (6S,9S,12S,15S,18S,24S,27S,30S,33S)-18,30-dibenzyl-12,24-diisobutyl-9,27-diisopropyl-2,2,5,6,11,17,23,26-octamethyl-33-(methyl((S)-1-oxo-1-(((S)-1-oxo-1-(piperidin-1-yl)propan-2-yl)amino)-3-phenylpropan-2-yl)carbamoyl)-4,7,10,13,16,19,22,25,28,31-decaoxo-15-((R)-1-(trityloxy)ethyl)-3-oxa-5,8,11,14,17,20,23,26,29,32-decaazapentatriacontan-35-oate (Compound SP-522) (42.9 mg, 22 umol) in dichloromethane (200 ul), and the mixture was stirred at room temperature for 10 minutes. The reaction solution was then concentrated under reduced pressure and purified by reverse phase silica gel column chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution=70/30→0/100) to afford the title compound (Compound SP-523) (11.7 mg, 33%).

Workup

  1. concentrationThe reaction solution was then concentrated under reduced pressure
  2. custompurified by reverse phase silica gel column chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution=70/30→0/100)

Sources & evidence

ORD record
ord-3bec474b22ff4c998d8087d890ec5f09
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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