1,2-Dichloroethane → Tert-butyl 3-(4-(3-nitropyridin-4-yl)piperazin-1-yl)-3-oxopropylcarbamate

HRID 69868

Reaction equation

HRID 69868 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][CH2:25][C:26](O)=[O:27])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl.CCOC(C)=O>[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:26](=[O:27])[CH2:25][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

7

Reactant 4

HCID 111,2-DichloroethaneHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 181649HOAtHCID 431140711-(3-Nitropyridin-4-yl)piperazine

Product 1

HCID 69044068Tert-butyl 3-(4-(3-nitropyridin-4-yl)piperazin-1-yl)-3-oxopropylcarbamateYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution containing 1.0 eq each of 1-(3-nitropyridin-4-yl)piperazine, N-Boc-beta-alanine, HOAT and EDC in DCM, at a concentration of 0.1 M, was stirred for 16 hours. The solution was diluted with EtOAc and was washed with H2O, Na2CO3(sat), NaCl(sat.), was dried over MgSO4, was filtered and the volatiles were removed in vacuo yielding tert-butyl 3-(4-(3-nitropyridin-4-yl)piperazin-1-yl)-3-oxopropylcarbamate (93%). LCMS (m/z): 379.9 (MH+); LC Rt=1.92 min.

Workup

  1. washwas washed with H2O, Na2CO3(sat), NaCl(sat.)
  2. dry with materialwas dried over MgSO4
  3. filtrationwas filtered
  4. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-15eb03f88afe4dd7b5b57a57fa19cdb4
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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