Water → HCID 117800780, compound

HRID 2200857Notes

Reaction equation

HRID 2200857 reaction equation
CC(C)(OC(=O)[NH:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][NH:42][C:43]([C:45]([CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])([CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][C:59]([OH:61])=[O:60])[C:46]([OH:48])=[O:47])=[O:44])C.C1C(=O)N(O[C:83]([C@@H:85]([NH:91][C:92]([O:94][CH2:95][C:96]2[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=2)=[O:93])[CH2:86][CH2:87][C:88]([NH2:90])=[O:89])=[O:84])C(=O)C1.CCN(C(C)C)C(C)C.O>C1COCC1.C(#N)C>[NH2:90][C:88](=[O:89])[CH2:87][CH2:86][C@@H:85]([C:83](=[O:84])[NH:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][NH:42][C:43]([C:45]([CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])([CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][C:59]([OH:61])=[O:60])[C:46]([OH:48])=[O:47])=[O:44])[NH:91][C:92](=[O:93])[O:94][CH2:95][C:96]1[CH:97]=[CH:98][CH:99]=[CH:100][CH:101]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 513418512,5-Dioxopyrrolidin-1-yl N~2~-[(benzyloxy)carbonyl]-L-glutaminateHCID 117800214HCID 117800214, compound

Product 1

HCID 117800780HCID 117800780, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-((2,2-Dimethyl-4-oxo-3,8,11,14,17,20,23,26,29,32, 35,38-dodecaoxa-5-azatetracontan-40-yl)carbamoyl)-2-undecyltridecanedioic acid (20 mg, 0.018 mmol) in THF (Volume: 2 mL) was added to Z-L-Gln-Osu (Santa Cruz Biotechnology, CAS 34078-85-8, 11 mg, 0.029 mmol), then DIPEA (75 μl, 0.429 mmol) was added. Stirred at room temperature under a nitrogen atmosphere over weekend. Complete conversion was observed by LCMS (Acidic Eluent A: Water+0.05% Trifluoroacetic Acid, Eluent B: ACN, column Sunfire C18 3.5 μm 3.0×30 mm −40° C., 5-95% gradient 2 minutes, retention time 1.77 min) The reaction mixture was concentrated under reduced pressure and then dissolved in acetonitrile. Purified on a MS-triggered HPLC (Sunfire 30×50 mm Sum column ACN/H2O w/0.1% TFA 75 ml/min 1.5 ml injection, 55-80% ACN 3.5 min gradient, retention time 2.70 minutes) and the fractions pooled and lyophilized to give 10.5 mg clean product ZQ-FA in 46% yield as a clear colorless oil.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. dissolutiondissolved in acetonitrile
  3. customPurified on a MS-triggered HPLC (Sunfire 30×50 mm Sum column ACN/H2O w/0.1% TFA 75 ml/min 1.5 ml injection, 55-80% ACN 3.5 min gradient, retention time 2.70 minutes)

Sources & evidence

ORD record
ord-ae5722c2ceb542e3a7e29dfa9ad3e74b
Source dataset
uspto-grants-2016_06
Patent number
US09359400B2

Reaction notes

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