Methanol → N2-(tert-butoxycarbonyl)-N6-(iminomethoxymethyl)-L-lysine tert-butyl ester hydrochloride

HRID 1975908Notes

Reaction equation

HRID 1975908 reaction equation
[C:1]([O:5][C:6](=[O:23])[C@H:7]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]#N)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[ClH:24].C(OC(=O)[C@H](CCCCNC=NOCC)[NH:32][C:33](OC(C)(C)C)=[O:34])(C)(C)C.Cl.C(OC(=O)[C@H](CCCNCOC=N)NC(OC(C)(C)C)=O)(C)(C)C.CO>ClCCl>[ClH:24].[C:1]([O:5][C:6](=[O:23])[C@H:7]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][O:34][CH:33]=[NH:32])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 54448533N2-(tert-butoxycarbonyl)-N6-(cyano)-L-lysine tert-butyl esterHCID 86583874N2-(tert-butoxycarbonyl)-N5-(iminomethoxymethyl)-L-ornithine tert-butyl ester hydrochlorideHCID 178475094HCID 178475094, compound

Product 1

HCID 86756656N2-(tert-butoxycarbonyl)-N6-(iminomethoxymethyl)-L-lysine tert-butyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

From 1.6 g (4.89 mmol) N2-(tert-butoxycarbonyl)-N6-(cyano)-L-lysine tert-butyl ester was prepared 1.5 g (75%) of foamy solid N2-(tert-butoxycarbonyl)-N6-(ethoxyiminomethyl)-L-lysine tert-butyl ester hydrochloride by the method described for N2-(tert-butoxycarbonyl)-N5-(iminomethoxymethyl)-L-ornithine tert-butyl ester hydrochloride. TLC (methanol:dichloromethane/1:9) Rf=0.36. Mass spectrum (CI) 360 (MH+, 60%).

Sources & evidence

ORD record
ord-fe3d865654e842d2a9289671a8cd7161
Source dataset
uspto-grants-2001_05
Patent number
US06225305B1

Reaction notes

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