Triethylamine → Boc-L-Lys(Z)-OMe

HRID 2302205Notes

Reaction equation

HRID 2302205 reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([OH:20])=[O:19])[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].[CH3:28]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>ClCCl.CO>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([O:20][CH3:28])=[O:19])[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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724765Boc-Lys(Z)-OHHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 11132998Boc-L-Lys(Z)-OMeYield 103%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Boc-Lys(Cbz)-OH (25 g) was dissolved in dichloromethane/methanol=9/1 v/v (500 ml). TBTU (21.1 g) was added and the solution adjusted to pH 8 by addition of triethylamine. The reaction mixture was stirred for 1 h at room temperature. The mixture was washed successively with cold 2N hydrogen chloride solution, water, 5% sodium hydrogencarbonate, and water. The organic layer was dried over sodium sulfate, filtered and evaporated. The residue was purified by chromatography on silica (eluent: ethyl acetate/heptane =1/4 v/v) to yield Boc-Lys(Cbz)-OMe (26.7 g). TLC: Rf=0.79, silica gel, ethyl acetate/heptane=3/1 v/v.

Workup

  1. washThe mixture was washed successively with cold 2N hydrogen chloride solution, water, 5% sodium hydrogencarbonate, and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography on silica (eluent: ethyl acetate/heptane =1/4 v/v)

Sources & evidence

ORD record
ord-24b979049c9d4655b9165d8b3618937f
Source dataset
uspto-grants-2002_08
Patent number
US06432921B1

Reaction notes

Loading…