1,1'-Carbonyldiimidazole → HCID 58560974, compound

HRID 2408152Notes

Reaction equation

HRID 2408152 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][C@@H:7]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C@@H:8]([C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH3:11])=[C:4]([C:30]#[N:31])[CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH2:45]([O:47][C:48](=[O:52])[CH2:49][CH2:50][NH2:51])[CH3:46]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][C@@H:7]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)[C@@H:8]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH:51][CH2:50][CH2:49][C:48]([O:47][CH2:45][CH3:46])=[O:52])=[O:17])=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH3:11])=[C:4]([C:30]#[N:31])[CH:3]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 58561010HCID 58561010, compound

Product 1

HCID 58560974HCID 58560974, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from step A was dissolved in THF (10 mL) then CDI (1.018 g, 6.28 mmol) was added. After being stirred for one hour, β-alanine ethyl ester hydrochloride (560 mg, 6.28 mmol) was added, then the mixture was stirred overnight at RT. The mixture was diluted with EtOAc then washed with water then brine. The organic layer was dried over MgSO4, filtered, then concentrated. The resulting residue was purified by silica gel chromatography to afford the title compound. 1H NMR (500 MHz, CD3OD): δ 7.72 (d, J=2.5 Hz, 1H); 7.67 (d, J=8.5 Hz, 2H); 7.50 (dd, J=9.0, 2.5 Hz, 1H); 7.37 (d, J=8.0 Hz, 2H); 7.24 (d, J=8.0 Hz, 2H); 7.13 (d, J=8.5 Hz, 2H); 6.81 (d, J=9.5 Hz, 1H); 5.63 (d, J=6.0 Hz, 1H); 4.12 (q, J=7.5 Hz, 2H); 3.61 (t, J=7.0 Hz, 2H); 3.19 (m, 1H); 2.62 (t, J=7.0 Hz, 2H); 2.00-1.94 (m, 1H); 1.73-1.67 (m, 1H); 1.22 (t, J=7.5 Hz, 3H); 1.19-1.16 (m, 2H); 0.83 (t, J=7.0 Hz, 3H). LC2 2.38 min. (M+H)+ 597.

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. washthen washed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c0f5bef88d4146398b4b0327d9ac3e46
Source dataset
uspto-grants-2014_08
Patent number
US08809579B2

Reaction notes

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