Triethylamine → Fmoc-Phe-Lys(Boc)-OtBu

HRID 1692611Notes

Reaction equation

HRID 1692611 reaction equation
[NH:1]([C:13]([O:15][CH2:16][CH:17]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[C@H:2]([C:10](O)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.ON1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1.C(N(CC)CC)C.[NH2:60][C@H:61]([C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[CH2:62][CH2:63][CH2:64][CH2:65][NH:66][C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68].Cl>ClCCl>[NH:1]([C:13]([O:15][CH2:16][CH:17]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[C@H:2]([C:10]([NH:60][C@H:61]([C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[CH2:62][CH2:63][CH2:64][CH2:65][NH:66][C:67]([O:69][C:70]([CH3:71])([CH3:72])[CH3:73])=[O:68])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 978331Fmoc-phenylalanineHCID 1381988513288-57-8

Product 1

HCID 67149928Fmoc-Phe-Lys(Boc)-OtBu

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of Fmoc-Phe-OH (6, 5.00 g, 12.9 mmol) in dichloromethane (100 mL) were added HOSu (1.56 g, 13.6 mmol) and DCC (2.93 g, 14.2 mmol). The resulting suspension was stirred at room temperature for 3 h. Then, triethylamine (1.83 mL, 13.2 mmol) and H-Lys(Boc)-OtBu.HCl (4.46 g, 13.2 mmol) were added consecutively, and the resulting suspension was stirred overnight. The reaction mixture was filtered, and the filtrate was washed with 10% aqueous citric acid, water, a saturated aqueous NaHCO3 solution, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. This gave crude 8 (8.97 g, max. 12.91 mmol, 100%) as a white solid. 1H NMR (300 MHz, CDCl3) δ: 1.10-1.90 (m, 6H, CH2-Lys), 1.41 (s, 18H, tBu), 3.01-3.15 (m, 4H, N—CH2-Lys+CH2-Phe), 4.19 (t, 1H, J=6.8 Hz, CH-Fmoc), 4.25-4.55 (m, 4H, 2×α-H+ CH2-Fmoc), 7.19-7.35 (m, 7H, HAr), 7.38 (t, 2H, J=7.4 Hz, HAr), 7.51 (m, 2H, HAr), 7.72 (d, 2H, J=7.5 Hz, HAr).

Workup

  1. stirringthe resulting suspension was stirred overnight
  2. filtrationThe reaction mixture was filtered
  3. washthe filtrate was washed with 10% aqueous citric acid, water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThis gave crude 8 (8.97 g, max. 12.91 mmol, 100%) as a white solid

Sources & evidence

ORD record
ord-b3c56f582682442e91e04d658c2147e3
Source dataset
uspto-grants-2012_04
Patent number
US08158590B2

Reaction notes

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