Trifluoroacetic acid → HCID 14828033, compound

HRID 592505Notes

Reaction equation

HRID 592505 reaction equation
[NH:1]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:2]([C:18]([NH:20][C@H:21]([C:37]([O:39][CH3:40])=[O:38])[CH2:22][CH2:23][CH2:24][CH2:25][NH:26]C(OCC1C=CC=CC=1)=O)=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OCC1C=CC=CC=1)=O.FC(F)(F)C(O)=O>CO>[NH:1]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:2]([C:18]([NH:20][C@H:21]([C:37]([O:39][CH3:40])=[O:38])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 14828031Boc-Lys(Z)-Lys(Z)-OMe

Product 1

HCID 14828033HCID 14828033, compoundYield 145.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dilysine 10 (7.43 g, 0.0113 mol) was dissolved in MeOH (100 mL). After being purged with nitrogen, 10% Pd/C (0.30 g) was added. The flask was then purged with hydrogen and the reaction mixture was stirred for overnight. The Pd/C was removed by filtration through a pad of celite. Trifluoroacetic acid (TFA, 1.8 mL, 0.023 mol) was added into the filtrate and then the solvent was removed in vacuo to give viscous oil. A white gluey substance was obtained by triturating with 20 mL diethyl ether. The resulting substance was dried in vacuo to give the glassy solid product 11 (6.4 g, 92%): 1H NMR (500 MHz, d6 DMSO) δ 8.19 (d, J=7.5, 1 H), 7.90 (br s, 6H), 6.82 (d, J=8.0, 1 H), 4.23 (m, 1H), 3.91 (m, 1H), 3.61 (s, 3H), 2.75 (m, 4H), 1.36-1.61 (m, 21H); 13C NMR (125 MHz, d6 DMSO) δ 172.4 (2), 158.4 (q, 2), 155.3, 117.2 (q, 2), 78.0, 53.9, 51.6, 38.7, 38.6, 31.2, 30.3, 28.1 (3), 26.7, 26.5, 22.3, 22.2; HRMS (FAB) m/z calcd for C22H38F6N4O9 (M+H)+ 389.2764, found 389.2767.

Workup

  1. customAfter being purged with nitrogen, 10% Pd/C (0.30 g)
  2. additionwas added
  3. customThe flask was then purged with hydrogen
  4. customThe Pd/C was removed by filtration through a pad of celite
  5. customthe solvent was removed in vacuo
  6. customto give viscous oil
  7. customA white gluey substance was obtained
  8. customby triturating with 20 mL diethyl ether
  9. customThe resulting substance was dried in vacuo

Sources & evidence

ORD record
ord-4b29b565f3f84912ac22f9621f58b24e
Source dataset
uspto-grants-2016_01
Patent number
US09238697B2

Reaction notes

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