Diisopropylethylamine → HCID 66713377, compound

HRID 2063450Notes

Reaction equation

HRID 2063450 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:49]([O:56][C:57]([N:59]1[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1)=[O:58])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C(Cl)Cl.O>[CH2:49]([O:56][C:57]([N:59]1[CH2:64][CH2:63][N:62]([C:6](=[O:8])[C@@H:2]([NH:1][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:3]([CH3:4])[CH3:5])[CH2:61][CH2:60]1)=[O:58])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 83693Boc-L-ValineHCID 643495Benzyl piperazine-1-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 66713377HCID 66713377, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Boc-(L)-Val-OH (2 g) in DCM (5 mL) was added DIPEA (4.7 mL) and HATU (5.2 g). After stirring at RT for 10 min, a solution of piperazine-1-carboxylic acid benzyl ester in DCM (5 mL) was added and the resulting reaction mixture was stirred at RT for 2 h. Water was added and the phases were separated. The org. phase was washed with brine, dried (MgSO4) and evaporated off to give 9.3 g of the desired compound as beige oil.

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at RT for 2 h
  3. customthe phases were separated
  4. washphase was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated off

Sources & evidence

ORD record
ord-d3e5682c0ff64ad8addb480f178f5c89
Source dataset
uspto-grants-2012_10
Patent number
US08288385B2

Reaction notes

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