Diisopropylethylamine → N5-[(Benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithyl-N5-[(benzyloxy)carbonyl]-N-(2-{[(benzyloxy)carbonyl]amino}ethyl)-L-ornithinamide

HRID 269644Notes

Reaction equation

HRID 269644 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH2:34]([O:41][C:42]([NH:44][CH2:45][CH2:46][CH2:47][C@@H:48]([C:57]([OH:59])=O)[NH:49][C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[CH2:60]([O:67][C:68](=[O:91])[NH:69][CH2:70][CH2:71][CH2:72][C@H:73]([NH2:90])[C:74]([NH:76][CH2:77][CH2:78][NH:79][C:80]([O:82][CH2:83][C:84]1[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=1)=[O:81])=[O:75])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>CN(C=O)C>[CH2:34]([O:41][C:42]([NH:44][CH2:45][CH2:46][CH2:47][C@@H:48]([C:57]([NH:90][C@H:73]([C:74]([NH:76][CH2:77][CH2:78][NH:79][C:80]([O:82][CH2:83][C:84]1[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=1)=[O:81])=[O:75])[CH2:72][CH2:71][CH2:70][NH:69][C:68]([O:67][CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[O:91])=[O:59])[NH:49][C:50]([O:52][C:53]([CH3:54])([CH3:55])[CH3:56])=[O:51])=[O:43])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 7269338(2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131727157HCID 131727157, compound

Product 1

HCID 86619431N5-[(Benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithyl-N5-[(benzyloxy)carbonyl]-N-(2-{[(benzyloxy)carbonyl]amino}ethyl)-L-ornithinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

350 mg (0.92 mmol) of HATU and 330 mg (2.56 mmol) of N,N-diisopropylethylamine are added to a solution of 320 mg (0.88 mmol) of N5-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithine and 350 mg (0.73 mmol) of benzyl{(4S)-4-amino-5-[(2-{[(benzyloxy)carbonyl]amino}ethyl)amino]-5-oxopentyl}carbamate (Example 122A) in 5 ml of anhydrous DMF at 0° C. The reaction mixture is stirred at RT for 15 h. The solvent is then evaporated and the residue is stirred with water, collected by filtration and dried under high vacuum.

Workup

  1. customThe solvent is then evaporated
  2. stirringthe residue is stirred with water
  3. filtrationcollected by filtration
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-fee326e019414238842ceb08553e05da
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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