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

HRID 2288926Notes

Reaction equation

HRID 2288926 reaction equation
[N:1]#[N:2].[C:3]([O:7][C:8](=[O:25])[C@H:9]([CH2:18][CH2:19][CH2:20][CH2:21][NH:22]C#N)[NH:10][C:11]([O:13][C:14](C)(C)C)=O)([CH3:6])([CH3:5])[CH3:4].N#N.[ClH:28].C(OC(=O)[C@H](CCCCNC=NOCC)[NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])(C)(C)C.N#N.Cl.C(OC(=O)[C@H](CCCNCOC=NC(OC(C)(C)C)=O)N)(C)(C)C.CO>ClCCl>[N:1]#[N:2].[ClH:28].[C:3]([O:7][C:8](=[O:25])[C@H:9]([CH2:18][CH2:19][CH2:20][CH2:21][NH2:22])[NH:10][CH2:11][O:13][CH:14]=[N:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])([CH3:4])([CH3:5])[CH3:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 86755535N2 (tert-butoxycarbonyl)-N5-(iminomethoxymethyl)-L-ornithine tert-butyl ester hydrochlorideHCID 131721879N2 (tert-butoxycarbonyl)-N6-(cyano)-L-lysine tert-butyl esterHCID 178475095HCID 178475095, compound

Product 1

HCID 131721877N2 (tert-butoxycarbonyl)-N2-(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-e69960578289401e952f5aef22f15d7f
Source dataset
uspto-grants-2000_07
Patent number
US06090846

Reaction notes

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