1,1'-Carbonyldiimidazole → HCID 66628638, compound

HRID 1807413Notes

Reaction equation

HRID 1807413 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]1[C@H:22]1[NH:27][C:26](=[O:28])[C@@H:25]([C@@H:29]([CH3:32])[CH2:30][CH3:31])[N:24]([CH:33]([C:44]2[N:45]=[C:46]([CH3:49])[O:47][CH:48]=2)[C:34](NC2C=CC=CC=2O)=[O:35])[C:23]1=[O:50]>ClCCl>[CH2:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13][CH:14]1[C@H:22]1[NH:27][C:26](=[O:28])[C@@H:25]([C@@H:29]([CH3:32])[CH2:30][CH3:31])[N:24]([CH:33]([C:44]2[N:45]=[C:46]([CH3:49])[O:47][CH:48]=2)[C:34]([OH:35])=[O:2])[C:23]1=[O:50]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 66628857HCID 66628857, compound

Product 1

HCID 66628638HCID 66628638, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbonyldiimidazole (352 mg, 1.6 equiv.) was added to a solution of 2-{(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-[(1S)-1-methylpropyl]-2,5-dioxo-1-piperazinyl}-N-(2-hydroxyphenyl)-2-(2-methyl-1,3-oxazol-4-yl)acetamide (11.8 g pre-dried in vacuo over P4O10 for 24 hours) in dichloromethane (20 mL) and the solution was left at room temperature for 16 hr. The mixture was evaporated and the residue dissolved in acetone (20 ml) and water (20 ml) added, followed by addition of 2NHCl (2 ml) and the mixture left at room temperature for 4.5 hr. This was extracted with ethylacetate (2×30 ml) and the combined organic phase dried via a hydrophobic frit and evaporated. The residue was taken up in ethylacetate (30 ml) washed with 2NHCl (2×10 ml) and then extracted with saturated sodium bicarbonate solution (2×15 ml). The combined aqueous phase was acidifed with 2NHCl and extracted with ethylacetate (2×20 ml) and the combined organic phase washed with brine dried via a hydrophobic frit and evaporated to give {(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-[(1S)-1-methylpropyl]-2,5-dioxo-1-piperazinyl}(2-methyl-1,3-oxazol-4-yl)acetic acid (0,355 mg, 73%) as a white solid.

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue dissolved in acetone (20 ml)
  3. additionwater (20 ml) added
  4. additionfollowed by addition of 2NHCl (2 ml)
  5. waitthe mixture left at room temperature for 4.5 hr
  6. extractionThis was extracted with ethylacetate (2×30 ml)
  7. customthe combined organic phase dried via a hydrophobic frit
  8. customevaporated
  9. washwashed with 2NHCl (2×10 ml)
  10. extractionextracted with saturated sodium bicarbonate solution (2×15 ml)
  11. extractionextracted with ethylacetate (2×20 ml)
  12. washthe combined organic phase washed with brine
  13. customdried via a hydrophobic frit
  14. customevaporated

Sources & evidence

ORD record
ord-34f6dc8d1ec94ea79a31958cb659bcf2
Source dataset
uspto-grants-2013_01
Patent number
US08357685B2

Reaction notes

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