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

HRID 379080Notes

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].C([O:28][C:29]([NH:31][C@H](C(O)=O)CCCCNC=NOCC)=O)(C)(C)C.CO.[Cl:48]CCl>>[ClH:48].[C:1]([O:5][C:6](=[O:23])[C@H:7]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][O:28][CH:29]=[NH:31])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 887Methanol

HCID 6344Dichloromethane

HCID 54448533N2-(tert-butoxycarbonyl)-N6-(cyano)-L-lysine tert-butyl ester

HCID 178475092HCID 178475092, compound

Product 1

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

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 tart-butyl ester hydrochloride by the method described for N2-(tert-butoxycarbonyl)-N5-(imonomethoxymethyl)-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-f5059cf59a654b4d81205b4e8bf7ef59
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06297276B1

Reaction notes

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