HCID 11294345, compound → HCID 87150482, compound

HRID 1096469Notes

Reaction equation

HRID 1096469 reaction equation
[C:1]([NH:5][C:6]([CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])([CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=[O:4])[CH:2]=[CH2:3].[CH3:34][N+:35]([O-:37])=[O:36].C(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[C:30]([O:29][C:27]([CH2:26][CH2:25][C:6]([NH:5][C:1](=[O:4])[CH:2]=[C:3]=[CH:34][N+:35]([O-:37])=[O:36])([CH2:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

4

Reactant 2

HCID 11294345HCID 11294345, compoundHCID 88822275HCID 88822275, compound

Product 1

HCID 87150482HCID 87150482, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of acryl amide 2 (2 g 4.2 mmol) in a MeNO2/CHCl3 mixture (1:1; 100 mL), TMG 200 μL) was added and maintained at 25° C. for 24 h. The mixture was then concentrated in vacuo to give a crude solid, which was dissolved in CHCl3 then sequentially washed with dilute aqueous HCl, water, and saturated brine. The organic solution was dried (Na2SO4), filtered, and concentrated in vacuo to give a crude oil, which was column chromatographed (SiO2) eluting with 25% ethyl acetate (EtOAc) in hexane to give (93%) amide 3, as a white solid: 2.1 g; mp 140-141° C.; 1H NMR δ 1.45 (s, 27H, CH3), 1.99 (t, 6H, J=7.5 Hz, CH2CH2CO), 2.24 (t, 6H, J=7.5 Hz, CH2CO), 2.26 (m, 4H, CH2CH2CO), 4.47 (t, 2H, J=6 Hz, O2NCH2), 6.19 (s, 1H, N); 13C NMR δ 22.8 (CH2CO), 27.7 (CH3), 29.6 (CH2CO), 29.8 (CH2CH2CO), 32.4 (O2NCH2CH2), 57.3 (NHC), 74.5 (O2NCH2), 80.2 (CMe3), 170.1 (CONH), 172.4 (CO2); IR 3300, 1710, 1670, 1552 cm−1; MS ESI; 553.3, Calculated 553.3 [M+Na+]. Analysis (C26H46N2O9) Found C, 57.94; H, 8.66; N, 5.20. Calculated C, 58.85; H, 8.74; N, 5.28.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customto give a crude solid, which
  3. washthen sequentially washed with dilute aqueous HCl, water, and saturated brine
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude oil, which
  8. customchromatographed (SiO2)
  9. washeluting with 25% ethyl acetate (EtOAc) in hexane

Sources & evidence

ORD record
ord-65bdcef6619249a6914e0ce41d76ba47
Source dataset
uspto-grants-2012_03
Patent number
US08138301B2

Reaction notes

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