Triethylamine → HCID 86675711, compound

HRID 1055185Notes

Reaction equation

HRID 1055185 reaction equation
[NH2:1][C@@H:2]([CH2:65][CH2:66][CH2:67][CH2:68][NH2:69])[C:3](=[O:64])[NH:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:63])[CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][C:37]([NH:39][CH2:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH2:47][CH2:48][O:49][CH2:50][CH2:51][CH2:52][NH:53][C:54](=[O:62])[C@@H:55]([NH2:61])[CH2:56][CH2:57][CH2:58][CH2:59][NH2:60])=[O:38].[C:70](Cl)(=[O:84])[CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83].C(N([CH2:91][CH3:92])CC)C>ClCCl>[O:64]=[C:3]([C@H:2]([NH:1][C:70](=[O:84])[CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:91][CH3:92])[CH2:65][CH2:66][CH2:67][CH2:68][NH:69][C:70](=[O:84])[CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83])[NH:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:63])[CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][C:37]([NH:39][CH2:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH2:47][CH2:48][O:49][CH2:50][CH2:51][CH2:52][NH:53][C:54](=[O:62])[C@H:55]([NH:61][C:70](=[O:84])[CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83])[CH2:56][CH2:57][CH2:58][CH2:59][NH:60][C:70](=[O:84])[CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83])=[O:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66986Myristoyl chlorideHCID 86675712HCID 86675712, compound

Product 1

HCID 86675711HCID 86675711, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N1,N19-bis((S)-16,20-diamino-15-oxo-4,7,10-trioxa-14-azaicosyl)-4,7,10,13,16-pentaoxanonadecane-1,19-diamide (synthesis previously described) was dissolved in dichloromethane and placed in an ice-bath. Myristoyl chloride was added followed by triethylamine. The ice-bath was removed and the reaction was allowed to stir overnight at room temperature under a blanket of inert gas. Next day, diluted with dichloromethane to 100 mL and washed with 1M HCl (75 mL), H2O (75 mL), saturated bicarbonate solution (75 mL) and saturated brine solution (75 mL). Back extracted all aqueous washes with dichloromethane (25 mL). Dried organics with MgSO4, filtered and concentrated. Purification by silica gel chromatography with a dichloromethane/methanol gradient yielded N1,N19-bis((R)-15,22-dioxo-16-tetradecanamido-4,7,10-trioxa-14,21-diaza-penta-triacontyl)-4,7,10,13,16-pentaoxanonadecane-1,19-diamide (410 mg). LCMS ESI+: m/z 1841 (M+H).

Workup

  1. customplaced in an ice-bath
  2. customThe ice-bath was removed
  3. additionNext day, diluted with dichloromethane to 100 mL
  4. washwashed with 1M HCl (75 mL), H2O (75 mL), saturated bicarbonate solution (75 mL) and saturated brine solution (75 mL)
  5. extractionBack extracted all aqueous washes with dichloromethane (25 mL)
  6. filtrationDried organics with MgSO4, filtered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography with a dichloromethane/methanol gradient

Sources & evidence

ORD record
ord-df065e81a34a40978847dea334bfae8d
Source dataset
uspto-grants-2016_07
Patent number
US09393315B2

Reaction notes

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