Diethyl Ether → Boc-L-Lys(Z)-OMe

HRID 477702Notes

Reaction equation

HRID 477702 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:25]([OH:27])=[O:26])[NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28](OCC)C.[N+](=C)=[N-]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:28][O:26][C:25](=[O:27])[C@H:16]([CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[NH:17][C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21584013Chloroform ethylacetateSolvent

Procedure

An ethyl 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: ##STR79##

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-18e4ae5619444184a029b15beb023680
Source dataset
uspto-grants-1989_12
Patent number
US04888427

Reaction notes

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