Diisopropylethylamine → HCID 131727154, compound

HRID 269635Notes

Reaction equation

HRID 269635 reaction equation
[CH3:1]N(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][C@H:47]([NH:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C:48]([OH:50])=O)=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C1(N[CH:66]2[CH2:71][CH2:70][CH2:69][CH2:68][CH2:67]2)CCCCC1.Cl.C([N:80]([CH2:84][CH2:85][NH2:86])[C:81](=[O:83])[OH:82])C1C=CC=CC=1>CN(C=O)C>[CH2:1]([O:82][C:81](=[O:83])[NH:80][CH2:84][CH2:85][NH:86][C:48](=[O:50])[C@@H:47]([NH:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[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])[C:66]1[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=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 19805659HCID 19805659, compoundHCID 45357173(2S)-4-{[(Benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]butanoic acid--N-cyclohexylcyclohexanamine (1/1)

Product 1

HCID 131727154HCID 131727154, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

321.9 mg (0.847 mmol) of HATU and 199.3 mg (1.534 mmol) of N,N-diisopropylethylamine are added to a solution of 410.8 mg (0.770 mmol) of (2S)-4-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]butanoic acid —N-cyclohexylcyclohexanamine (1:1) in 25 ml of anhydrous DMF. After stirring at RT for 15 min, 195.3 mg (0.847 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-def6590a91bb4b1baccc72fd5e79dee6
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

Loading…