Triethylamine → HCID 59176533, compound

HRID 628690Notes

Reaction equation

HRID 628690 reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2](C(O)=O)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].O.[OH:29][C:30]1C2N=NNC=2C=CC=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.[NH2:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][N:60]=1>CN(C)C=O.C([O-])(O)=O.[Na+]>[C:24]([O:23][C:21]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH:7][C:8](=[O:9])[O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:30](=[O:29])[NH:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][N:60]=1)=[O:22])([CH3:25])([CH3:26])[CH3:27]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 195092-PyridinemethanamineHCID 2724765Boc-Lys(Z)-OHHCID 178526939HCID 178526939, compound

Product 1

HCID 59176533HCID 59176533, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of Boc-Lys(Z)—OH (Bachem, 10.0 g, 26.3 mmol) in dimethylformamide (80 mL) was added hydroxybenzotriazole-hydrate (4.3 g, 31.6 mmol), triethylamine (7.3 mL, 52.6 mmol) and EDAC (6.1 g, 31.6 mmol). After stirring at 0° C. for 1 h, 2-aminomethylpyridine (3.0 mL, 28.9 mmol) was added to the mixture. The mixture was warmed to room temperature and stirred for an additional 17 h. The mixture was diluted with aqueous saturated NaHCO3 and extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (0% to 5% methanol/CHCl3) to afford the desired product 27: 1H NMR (d6-DMSO) δ 8.43 (d, J=4.0 Hz, 1H), 8.39 (t, J=5.6 Hz, 1H), 7.68 (t, J=7.6 Hz, 1H), 7.34-7.19 (m, 8H), 6.94 (d, J=7.6 Hz, 1H), 4.96 (s, 2H), 4.31 (d, J=5.6 Hz, 2H), 3.90-3.83 (m, 1H), 2.95-2.90 (m, 2H), 1.60-1.25 (m, 6H), 1.35 (s, 9H); ESI+ MS: m/z (rel intensity) 471.2 (100, [M+H]+).

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred for an additional 17 h
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by silica gel chromatography (0% to 5% methanol/CHCl3)

Sources & evidence

ORD record
ord-f57cfc3871694fa79bbb4259edf57031
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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