Diisopropylethylamine → HCID 178454188, compound

HRID 269628Notes

Reaction equation

HRID 269628 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][C:45](=[NH:62])[NH:46][CH2:47][CH2:48][CH2:49][C@@H:50]([C:59]([OH:61])=O)[NH:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.Cl.[NH2:64][CH2:65][CH2:66][NH:67][C:68](=[O:77])[O:69][CH2:70][C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1>CN(C=O)C>[CH2:70]([O:69][C:68](=[O:77])[NH:67][CH2:66][CH2:65][NH:64][C:59](=[O:61])[C@H:50]([CH2:49][CH2:48][CH2:47][NH:46][C:45]([NH:44][C:42]([O:41][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:43])=[NH:62])[NH:51][C:52]([O:54][C:55]([CH3:56])([CH3:57])[CH3:58])=[O:53])[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12715871Benzyl N-(2-aminoethyl)carbamate hydrochlorideHCID 178454189HCID 178454189, compound

Product 1

HCID 178454188HCID 178454188, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

419.3 mg (1.1 mmol) of HATU and 258.5 mg (2 mmol) of N,N-diisopropylethylamine are added to a solution of 408.4 mg (1 mmol) of N5-[{[(benzyloxy)carbonyl]amino}(imino)methyl]-N2-(tert-butoxycarbonyl)-L-ornithine in 15 ml of anhydrous DMF. After stirring at RT for 15 min, 253.76 mg (1.1 mmol) of benzyl (2-aminoethyl)carbamate hydrochloride are added. The reaction mixture is stirred at RT for 15 h. The solvent is then evaporated and the residue is taken up in dichloromethane. The organic phase is washed with water, dried over magnesium sulfate and concentrated. The crude product is purified by preparative HPLC.

Workup

  1. stirringThe reaction mixture is stirred at RT for 15 h
  2. customThe solvent is then evaporated
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-ec7a7be79b97436e8f1719310fd2847e
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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