N2-(tert-butoxycarbonyl)-N5-cyano-L-ornithine tert-butyl ester → HCID 178475096, compound

HRID 1975904Notes

Reaction equation

HRID 1975904 reaction equation
[ClH:1].[C:2]([O:6]C(=O)[C@H](CCCNCOC=N)NC(OC(C)(C)C)=O)(C)(C)[CH3:3].[C:26]([O:30][C:31](=[O:47])[C@H:32]([CH2:41][CH2:42][CH2:43][NH:44][C:45]#[N:46])[NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])([CH3:29])([CH3:28])[CH3:27].C(OC(=O)[C@H](CCCNC#N)N)(C)(C)C>>[ClH:1].[C:26]([O:30][C:31](=[O:47])[C@H:32]([CH2:41][CH2:42][CH2:43][NH:44][CH:45]=[N:46][O:6][CH2:2][CH3:3])[NH:33][C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])([CH3:27])([CH3:28])[CH3:29]

Participants

4

Reactant 3

HCID 11141515N2-(tert-butoxycarbonyl)-N5-cyano-L-ornithine tert-butyl esterHCID 86583874N2-(tert-butoxycarbonyl)-N5-(iminomethoxymethyl)-L-ornithine tert-butyl ester hydrochlorideHCID 86756654N5-cyano-L-ornithine tert-butyl ester

Product 1

HCID 178475096HCID 178475096, compoundYield 75%

Procedure

By a method described above for the preparation of N2-(tert-butoxycarbonyl)-N5-(iminomethoxymethyl)-L-ornithine tert-butyl ester hydrochloride, 1.05 g (3.35 mmol) of N2-(tert-butoxycarbonyl)-N5-cyano-L-ornithine tert-butyl ester produced 0.95 g (75%) N2-(tert-butoxycarbonyl)-N5-(ethoxyiminomethyl)-L-ornithine tert-butyl ester hydrochloride (TLC, silica gel, methanol:dichloromethane/1:4, Rf=0.61) and 1.195 g (3.2 mmol) of N2-tert-butoxycarbonyl)-N5-cyano-L-ornithine tert-butyl ester produces 0.63 g (63%) N2-(tert-butoxycarbonyl)-N5-(iminoisopropoxymethyl)-L-ornithine tert-butyl ester hydrochloride (TLC, silica gel, methanol:dichloro methane/1:4, Rf=0.53). Mass Spectrum (CI) 360 (MH+, 100%).

Sources & evidence

ORD record
ord-0c29aa1f63654d58aedee25f76427ab4
Source dataset
uspto-grants-2001_05
Patent number
US06225305B1

Reaction notes

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