1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 88120616, compound

HRID 480548Notes

Reaction equation

HRID 480548 reaction equation
C1CCN2C(=NCCC2)CC1.[C:12]1([CH2:18][O:19][C:20](=[O:60])[CH2:21][N:22]2[CH2:33][CH2:32][N:31]([CH2:34][C:35]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:36])[CH2:30][CH2:29][N:28]([CH2:45][C:46]([O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[O:47])[CH2:27][CH2:26][N:25]([CH2:56][C:57]([OH:59])=[O:58])[CH2:24][CH2:23]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Br[CH2:62][C:63]([N:65]([CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH3:101])[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83])=[O:64]>C1(C)C=CC=CC=1>[C:12]1([CH2:18][O:19][C:20](=[O:60])[CH2:21][N:22]2[CH2:23][CH2:24][N:25]([CH2:56][C:57]([O:59][CH2:62][C:63]([N:65]([CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83])[CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH3:101])=[O:64])=[O:58])[CH2:26][CH2:27][N:28]([CH2:45][C:46]([O:48][CH2:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)=[O:47])[CH2:29][CH2:30][N:31]([CH2:34][C:35]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[O:36])[CH2:32][CH2:33]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11193219{4,7,10-Tris[2-(benzyloxy)-2-oxoethyl]-1,4,7,10-tetraazacyclododecan-1-yl}acetic acidHCID 18764645HCID 18764645, compound

Product 1

HCID 88120616HCID 88120616, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

DBU (820 μL; 5.5 mmol) was added to a suspension of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid tris(phenylmethyl)ester (prepared according to Step E3 of Example 17) (3.71 g; 5.5 mmol) in toluene (350 mL) obtaining a clear solution, then 2-bromo-N,N-dioctadecylacetamide (prepared according to Example 5, Step A) (3.9 g; 6.05 mmol) dissolved in toluene (50 mL) was added dropwise. After 2 h the reaction mixture was filtered and the solvent was evaporated. The crude was suspended in CH3CN (50 mL) and the insoluble was filtered off with a paper filter. The solution was evaporated obtaining the desired product (4.63 g; 3.74 mmol). Yield 68%. The 13C-NMR, MS and IR spectra were consistent with the structure.

Workup

  1. customobtaining a clear solution
  2. additionwas added dropwise
  3. filtrationAfter 2 h the reaction mixture was filtered
  4. customthe solvent was evaporated
  5. filtrationthe insoluble was filtered off with a paper
  6. filtrationfilter
  7. customThe solution was evaporated

Sources & evidence

ORD record
ord-0babd302d29e4562903eebfd0a352948
Source dataset
uspto-grants-2003_11
Patent number
US06652834B2

Reaction notes

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