Diethyl Ether → Boc-L-Lys(Z)-OMe

HRID 1090001Notes

Reaction equation

HRID 1090001 reaction equation
[CH2:1](OCC)C.[CH2:6]([O:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C@@H:21]([C:30]([OH:32])=[O:31])[NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N+](=C)=[N-]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:31][C:30](=[O:32])[C@H:21]([CH2:20][CH2:19][CH2:18][CH2:17][NH:16][C:14]([O:13][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:15])[NH:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 9550DiazomethaneHCID 2724765Boc-Lys(Z)-OH

Product 1

HCID 11132998Boc-L-Lys(Z)-OMe

Reagents, catalysts & solvents 1

HCID 21584013Chloroform ethylacetateSolvent

Procedure

An ethyl ether solution of 1.48 g (3.9 mmol) of Nε -benzyloxycarbonyl-Nα -(tert-butoxycarbonyl)-L-lysine was combined with an ethyl ether solution of diazomethane at 0° C. The reaction mixture was evaporated to give a colorless oil in nearly quantitative yield (1.54 g). TLC Rf =0.38 (chloroform/ethyl acetate, 5:1). IR (neat) ν 3340, 1710, 1530 cm-1. NMR (CDCl3) δ 7.3 (5H, s), 7.25 (1H, m), 5.05 (2H, s), 5.0 (1H, m), 4.1 (1H, m), 3.8 (3H, s), 3.1 (2H, m), 2.0-1.1 (6H, m), 1.4 (9H, s). The product has the structural formula: ##STR82##

Workup

  1. customThe reaction mixture was evaporated
  2. customto give a colorless oil in nearly quantitative yield (1.54 g)

Sources & evidence

ORD record
ord-97dc652a6fd84597abd1db3e6d8db2a6
Source dataset
uspto-grants-1992_01
Patent number
US05079366

Reaction notes

Loading…