N-(tert-butoxycarbonyl)glycine → Tert-butyl 2-(4-(3-nitropyridin-4-yl)piperazin-1-yl)-2-oxoethylcarbamate

HRID 69869Notes

Reaction equation

HRID 69869 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)([O-:3])=[O:2].[C:16]([NH:23][CH2:24][C:25](O)=[O:26])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>>[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][N:13]([C:25](=[O:26])[CH2:24][NH:23][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:12][CH2:11]1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 431140711-(3-Nitropyridin-4-yl)piperazine

Product 1

HCID 69041507Tert-butyl 2-(4-(3-nitropyridin-4-yl)piperazin-1-yl)-2-oxoethylcarbamateYield 99%

Procedure

Following the method of Example 84 (Method 3), 1-(3-nitropyridin-4-yl)piperazine was coupled to N-Boc-glycine yielding tert-butyl 2-(4-(3-nitropyridin-4-yl)piperazin-1-yl)-2-oxoethylcarbamate (99% yield). LCMS (m/z): 365.8 (MH+); LC Rt=1.81 min.

Sources & evidence

ORD record
ord-ff1353cb7abf4fd9b1a4615066989560
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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