Boc-Lys(Z)-Lys(Boc)-Lys(Z)-OMe → HCID 101379021, compound

HRID 592506Notes

Reaction equation

HRID 592506 reaction equation
[NH:1]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[C@H:2]([C:18]([NH:20][C@H:21]([C:34]([NH:36][C@H:37]([C:53]([O:55][CH3:56])=[O:54])[CH2:38][CH2:39][CH2:40][CH2:41][NH:42]C(OCC1C=CC=CC=1)=O)=[O:35])[CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OCC1C=CC=CC=1)=O>CO.C(Cl)Cl.[Pd]>[NH:1]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[C@H:2]([C:18]([NH:20][C@H:21]([C:34]([NH:36][C@H:37]([C:53]([O:55][CH3:56])=[O:54])[CH2:38][CH2:39][CH2:40][CH2:41][NH2:42])=[O:35])[CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

5

Reactant 1

HCID 131734553Boc-Lys(Z)-Lys(Boc)-Lys(Z)-OMe

Product 1

HCID 101379021HCID 101379021, compoundYield 101.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 12 (0.88 g, 0.99 mmol) in MeOH (25 mL) and DCM (25 mL), was added Pd/C (0.20 g). This solution was flushed with H2 for 30 min. and then fitted with an H2 balloon. The reaction was allowed to proceed for 8 h at which time the mixture was filtered through celite, and conc. in vacuo to yield pure clear product 13 (0.622 g, quantitative): 1H NMR (500 MHz, d6 DMSO) δ 8.42 (br s, 1H), 8.16 (br s, 4H), 7.92 (br s, 1H), 6.92 (br s, 1H), 6.74 (br s, 1H), 4.27 (br s, 1H), 4.20 (br s, 1H), 3.89 (br s, 1H), 3.62 (s, 3H), 3.46 (br s, 3H), 2.87-2.73 (m, 5H), 2.52 (s, 1H), 1.80-1.45 (br s, 10H), 1.45-1.15 (m, 22H); 13C NMR (125 MHz, d6 DMSO) δ 173.2, 172.8, 156.4, 156.2, 78.94, 78.19, 54.91, 53.1, 52.7, 52.6, 39.3, 39.2, 32.8, 32.0, 30.9, 29.1, 29.1, 27.3, 27.2, 23.2, 23.1. HRMS (FAB) m/z calcd for C29H56N6O8 (M+H)+ 617.4238, found 617.4236.

Workup

  1. customThis solution was flushed with H2 for 30 min.
  2. customfitted with an H2 balloon
  3. filtrationthe mixture was filtered through celite

Sources & evidence

ORD record
ord-c1ef9c05a5904828a9285fd9cba6fc88
Source dataset
uspto-grants-2016_01
Patent number
US09238697B2

Reaction notes

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