1,1'-Carbonyldiimidazole → HCID 58468263, compound

HRID 2408150Notes

Reaction equation

HRID 2408150 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([OH:22])[C@@H:9]([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH2:36]([O:38][C:39](=[O:43])[CH2:40][CH2:41][NH2:42])[CH3:37]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([OH:22])[C@@H:9]([C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:42][CH2:41][CH2:40][C:39]([O:38][CH2:36][CH3:37])=[O:43])=[O:18])=[CH:20][CH:21]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 58468270HCID 58468270, compound

Product 1

HCID 58468263HCID 58468263, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of Step C (5.00 g, 15.7 mmol) in THF (100 mL) was added CDI (3.05 g, 18.82 mmol). After stirring at room temperature for one hour, β-alanine ethyl ester hydrochloride (3.61 mg, 23.53 mmol) was added, then the mixture was stirred at room temperature for two days. The mixture was diluted with EtOAc then washed with 1N NaOH, then water, then brine. The organic layer was dried over MgSO4, filtered, then concentrated to provide the title compound which was used without further purification. 1H NMR (499 MHz, CDCl3): δ 7.74 (d, J=7.9 Hz, 2H); 7.32 (d, =8.2 Hz, 2H); 7.28 (t, J=4.0 Hz, 2H); 7.25-7.15 (m, 2H); 6.88 (brs, 1H); 4.77 (d, 0.1=7.7 Hz, 1H); 4.20 (q, J=7.1 Hz, 2H); 3.75 (q, J=5.9 Hz, 2H); 2.89 (ddd, J=11.1, 7.7, 4.1 Hz, 1H); 2.66 (1, J=5.8 Hz, 2H); 1.47-1.37 (m, 2H); 1.30 (t, J=7.1 Hz, 3H); 1.11 (m, 2H); 0.76 (t, J=7.3 Hz, 3H). LC-MS: LC1 1.14 min. (M+H)+ 418.

Workup

  1. stirringthe mixture was stirred at room temperature for two days
  2. washthen washed with 1N NaOH
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6f42c2fc488d4de4a776fe3027f63aa8
Source dataset
uspto-grants-2014_08
Patent number
US08809579B2

Reaction notes

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