N2 (tert-butoxycarbonyl)-N5-cyano-L-ornithine tert-butyl ester → HCID 178475097, compound

HRID 2288922Notes

Reaction equation

HRID 2288922 reaction equation
[N:1]#[N:2].[ClH:3].[C:4]([O:8]C(=O)[C@H](CCCNCOC=NC(OC(C)(C)C)=O)N)(C)(C)[CH3:5].N#N.[C:30]([O:34][C:35](=[O:51])[C@H:36]([CH2:45][CH2:46][CH2:47][NH:48][C:49]#[N:50])[NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])([CH3:33])([CH3:32])[CH3:31]>>[N:1]#[N:2].[ClH:3].[C:30]([O:34][C:35](=[O:51])[C@H:36]([CH2:45][CH2:46][CH2:47][NH:48][CH:49]=[N:50][O:8][CH2:4][CH3:5])[NH:37][C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])([CH3:31])([CH3:32])[CH3:33].[N:1]#[N:2].[C:30]([O:34][C:35](=[O:51])[C@H:36]([CH2:45][CH2:46][CH2:47][NH:48][C:49]#[N:50])[NH:37][C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])([CH3:31])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 86755534N2 (tert-butoxycarbonyl)-N5-cyano-L-ornithine tert-butyl esterHCID 86755535N2 (tert-butoxycarbonyl)-N5-(iminomethoxymethyl)-L-ornithine tert-butyl ester hydrochloride

Product 2

HCID 86755534N2 (tert-butoxycarbonyl)-N5-cyano-L-ornithine tert-butyl esterHCID 178475097HCID 178475097, compoundYield 75%

Procedure

By the 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 produced 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-ecf4dbd1f33949ba8b717cbc9eeb3269
Source dataset
uspto-grants-2000_07
Patent number
US06090846

Reaction notes

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