1,1'-Carbonyldiimidazole → HCID 10416128, compound

HRID 2396607Notes

Reaction equation

HRID 2396607 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([O:20][N:21]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:22](=[O:28])[CH2:23][CH2:24][C:25]([OH:27])=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.Cl.[CH2:44]([O:51][NH:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][NH2:58])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(Cl)Cl>[CH2:13]([O:20][N:21]([C:22](=[O:28])[CH2:23][CH2:24][C:25](=[O:27])[NH:58][CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][NH:52][O:51][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 10250893HCID 10250893, compoundHCID 86749264HCID 86749264, compound

Product 1

HCID 10416128HCID 10416128, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Carbonyldiimidazole (CDI, 0.592 g, 3.65 mmol) was added to (8) (1.42 g, 3.48 mmol) in dry CH2Cl2 (90 mL) . After stirring for 1 hour, the solution was cooled to 0° C. and (6) (free amine, 0.74 g, 3.55 mmol) in CH2Cl2 (65 mL) was added by cannula over 5 minutes. After stirring for 12 hours (0° C. to room temperature), solvent was removed by rotary evaporation. Dilute brine (200 mL) was added, followed by extraction with EtOAc (4×100 mL). The organic phase was washed with 100 mL portions of cold 0.5M citric acid, 5% NaHCO3 and brine. Solvent removal led to 2.2 g (quantitative) of (9) as an oil, which was used directly in the next step. An analytical sample was chromatographed on silica gel, eluting with 3.5% EtOH/CHCl3 : 300 MHz NMR δ 1.1-1.7 (m+s, 21 H), 2.3-3.3 (m, 10 H), 3.60 (t, 2 H, J=7), 4.6 (br s, 1 H), 4.67 (s, 2 H), 4.80 (s, 2 H), 6.0 (br s, 1 H), 7.25-7.40 (m, 10 H). Anal. calcd. for C33H50N4O6 : C, 66.19; H, 8.42; N, 9.36. Found: C, 66.27; H, 8.40; N, 9.33.

Workup

  1. stirringAfter stirring for 12 hours (0° C. to room temperature), solvent
  2. customwas removed by rotary evaporation
  3. additionDilute brine (200 mL) was added
  4. extractionfollowed by extraction with EtOAc (4×100 mL)
  5. washThe organic phase was washed with 100 mL portions of cold 0.5M citric acid, 5% NaHCO3 and brine
  6. customSolvent removal
  7. customAn analytical sample was chromatographed on silica gel
  8. washeluting with 3.5% EtOH/CHCl3

Sources & evidence

ORD record
ord-d1dc4fab263140f08cb62e4e167f3740
Source dataset
uspto-grants-1996_02
Patent number
US05493053

Reaction notes

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