1,1'-Carbonyldiimidazole → HCID 10056534, compound

HRID 2396609Notes

Reaction equation

HRID 2396609 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:13]([O:20][N:21]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:62])[CH2:36][CH2:37][C:38](=[O:61])[N:39]([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][NH:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C:22](=[O:28])[CH2:23][CH2:24][C:25](O)=[O:26])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.Cl.[CH2:65]([O:72][NH:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][NH2:79])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1>C(Cl)Cl>[C:49]([O:48][C:46]([NH:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][N:39]([O:53][CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[C:38](=[O:61])[CH2:37][CH2:36][C:35](=[O:62])[NH:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][N:21]([O:20][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:22](=[O:28])[CH2:23][CH2:24][C:25](=[O:26])[NH:79][CH2:78][CH2:77][CH2:76][CH2:75][CH2:74][NH:73][O:72][CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)=[O:47])([CH3:51])([CH3:50])[CH3:52]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 10101221HCID 10101221, compoundHCID 86749264HCID 86749264, compound

Product 1

HCID 10056534HCID 10056534, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

CDI (0.188 g, 1.16 mmol) was added to a solution of (10) (0.76 g, 1.09 mmol) in dry CH2Cl2 (45 mL). The solution was cooled to 0° C. after 1 hour and (6) (free amine, 0.240 g, 1.15 mmol) was added by cannula in CH2Cl2 (60 mL) over 5 minutes. The reaction was stirred at 0° C. to room temperature for 24 hours. Solvent was removed in vacuo and dilute brine (100 mL) was added to the residue. Extraction was carried out with EtOAc (5×75 mL), followed by washing with 50 mL of cold 0.5M citric acid, 5% NaHCO3, water and brine. Solvent removal gave 0.87 g (90% ) of (11) which was used directly in the next reaction: NMR δ 1.1-1.8 (m+s, 27 H) , 2.3-3.7 (m, 20 H), 4.5 (br s, 1 H), 4.67 (s, 2 H), 4.82 (s, 4 H), 6.2 (br s, 1 H), 7.2-7.4 (m, 15 H). An analytical sample of (11) was obtained from silica gel column chromatography, eluting with 5% MeOH/CHCl3. Anal. calcd. for C49H72N6O9 : C, 66.19; H, 8.16; N, 9.45. Found: C, 66.18; H, 8.17; N, 9.42.

Workup

  1. customSolvent was removed in vacuo and dilute brine (100 mL)
  2. additionwas added to the residue
  3. extractionExtraction
  4. washby washing with 50 mL of cold 0.5M citric acid, 5% NaHCO3, water and brine
  5. customSolvent removal

Sources & evidence

ORD record
ord-823443919aac403aba8f6f2f096e1c83
Source dataset
uspto-grants-1996_02
Patent number
US05493053

Reaction notes

Loading…