Diethylamine → Lys(Mtr)

HRID 1883293Notes

Reaction equation

HRID 1883293 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:22]([OH:24])=[O:23])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[C:20]([CH3:21])=[C:18]([CH3:19])[C:15]([O:16][CH3:17])=[CH:14][C:12]=1[CH3:13])(=[O:10])=[O:9].C(NCC)C>C(Cl)Cl.C(#N)C>[NH2:1][C@H:2]([C:22]([OH:24])=[O:23])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[C:20]([CH3:21])=[C:18]([CH3:19])[C:15]([O:16][CH3:17])=[CH:14][C:12]=1[CH3:13])(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 131724478Fmoc-Lys(Mtr)

Product 1

HCID 15662507Lys(Mtr)

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

Fmoc-Lys(Mtr) 1 (5.25 g, 8.19 mmol) in 1:1 methylene chloride/acetonitrile (80 mL) at rt was treated with diethylamine (80 mL). After 1.5 h the solvents were evaporated. The residue was flushed with acetonitrile (2×50 mL) at 60° C., and then triturated with ether (80 mL). The resulting solid was collected by filtration, washed with ether, and then dissolved as far as possible in 1:1 methylene chloride/methanol. Some solid byproduct was removed by filtration and the filtrate was concentrated invacuo. The resulting light tan solid was dried in vacuo for 4 h (3.2221 g, 94%). 1H-NMR (DMSO-d6) δ 1.34, 1.57 and 1.72 (m, 6H), 2.05 (m, 2H), 3.38 (m, 1H), 3.68 (s, 3H), 3.71 (d, 2H), 7.03-7.40 (m, 12H). MS (FAB) 419.2 (MH)+, 441.4 (M+Na)+, 457.4 (M+K)+. MS (FAB) 419.2 (MH)+, 441.4 (M+Na)+, 457.4 (M+K)+.

Workup

  1. customAfter 1.5 h the solvents were evaporated
  2. customThe residue was flushed with acetonitrile (2×50 mL) at 60° C.
  3. customtriturated with ether (80 mL)
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with ether
  6. dissolutiondissolved as far as possible in 1:1 methylene chloride/methanol
  7. customSome solid byproduct was removed by filtration
  8. concentrationthe filtrate was concentrated invacuo
  9. customThe resulting light tan solid was dried in vacuo for 4 h (3.2221 g, 94%)

Sources & evidence

ORD record
ord-4739a9b00104493fa74b47567ba7586a
Source dataset
uspto-grants-2004_07
Patent number
US06759509B1

Reaction notes

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