1,1'-Carbonyldiimidazole → HCID 66628638, compound

HRID 655589Notes

Reaction equation

HRID 655589 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-16417ad1f75a4716bd356b2432280446
Source dataset
uspto-grants-2011_12
Patent number
US08071594B2

Reaction notes

Loading…