HCID 11068117, compound → HCID 10874022, compound

HRID 1793124Notes

Reaction equation

HRID 1793124 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11](I)[NH:12][C:13]=1[CH2:14][CH2:15][CH3:16])=[O:8]>CO>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]([C:11]2[NH:12][C:13]([CH2:14][CH2:15][CH3:16])=[C:9]([C:7]([NH:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[O:8])[N:10]=2)[NH:12][C:13]=1[CH2:14][CH2:15][CH3:16])=[O:8]

Participants

3

Reactant 1

HCID 11068117HCID 11068117, compound

Product 1

HCID 10874022HCID 10874022, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Iodide 6e (0.55 g; 1.6 mmol) was used as starting material. After cooling to rt, the reaction mixture was diluted with CH3OH and filtered. The filtrate was evaporated under vacuum, and the residue was recrystallized from EtOAc to afford 0.13 g (33%) of 1e as colorless prisms. mp>260 C; TLC (EtOAc): Rf=0.31; 1H NMR (CDCl3): δ 0.91 (t, 6H), 1.65 (m, 4H), 1.82 (m, 44), 3.00 (t, 4H), 3.34 (s, 6H), 3.48 (m, 8H), 7.29 (br t, 2H); 13C NMR (DMSO-d6): δ 14.3, 24.1, 26.7, 32.3, 61.9, 72.3, 137.5, 145.1, 167.3; UV/vis (CH3OH): max (M−1cm−1)=287 (25600), 295 (25400), 309 (13800); LRMS (CI+): m/z (%): 449 (100) [M+H]+; HRMS (CI+): calcd for C22H37N6O4 449.2876; found 449.2875; Anal. calcd for C22H36N6O4: C, 58.91; H, 8.09; N, 18.74; found: C, 59.00; H, 8.09; N, 18.78.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated under vacuum
  3. customthe residue was recrystallized from EtOAc

Sources & evidence

ORD record
ord-caba9355756548b0a75c50b05894c6a7
Source dataset
uspto-grants-2006_07
Patent number
US07078528B2

Reaction notes

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