Diisopropylethylamine → HCID 86624503, compound

HRID 269632Notes

Reaction equation

HRID 269632 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25](N(CC)C(C)C)(C)[CH3:26].[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.Cl.C([N:68]([C@H:72]([CH2:77][C:78]([NH:80][CH2:81][CH2:82][NH:83][C:84]([O:86][CH2:87][C:88]1[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=1)=[O:85])=[O:79])[CH2:73][CH2:74][CH2:75][NH2:76])[C:69](=[O:71])[OH:70])C1C=CC=CC=1>CN(C=O)C>[CH2:87]([O:86][C:84](=[O:85])[NH:83][CH2:82][CH2:81][NH:80][C:78](=[O:79])[CH2:77][C@@H:72]([NH:68][C:69]([O:70][CH2:10][C:11]1[CH:26]=[CH:25][CH:14]=[CH:13][CH:12]=1)=[O:71])[CH2:73][CH2:74][CH2:75][NH:76][C:57](=[O:59])[C@H:48]([CH2:47][CH2:46][CH2:45][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:49][C:50]([O:52][C:53]([CH3:54])([CH3:55])[CH3:56])=[O:51])[C:88]1[CH:89]=[CH:90][CH:91]=[CH:92][CH:93]=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 69216382HCID 69216382, compound

Product 1

HCID 86624503HCID 86624503, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

89.5 mg (0.235 mmol) of HATU and 55.3 mg (0.428 mmol) of N,N-diisopropylethylamine are added to a solution of 78.4 mg (0.214 mmol) of N5-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithine in 5 ml of anhydrous DMF. After stirring at RT for 15 min, a solution of 116 mg (0.235 mmol) of benzyl((1S)-4-amino-1-{2-[(2-{[(benzyloxy)carbonyl]amino}ethyl)amino]-2-oxoethyl}butyl)carbamate hydrochloride (Example 105A) in 5 ml of anhydrous DMF is 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-26c96ae642404579bb6d0beb581adc2f
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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