Diisopropylethylamine → HCID 18752836, compound

HRID 1838764Notes

Reaction equation

HRID 1838764 reaction equation
C(N(C(C)C)C(C)C)C.[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([OH:29])=O)=[CH:21][CH:20]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:54]([O:61][C:62]([N:64]1[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]1)=[O:63])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>CN(C=O)C.C(OCC)(=O)C.O>[CH2:54]([O:61][C:62]([N:64]1[CH2:69][CH2:68][N:67]([C:27](=[O:29])[CH2:26][CH2:25][C:22]2[CH:21]=[CH:20][C:19]([CH2:18][NH:17][C:15]([O:14][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:16])=[CH:24][CH:23]=2)[CH2:66][CH2:65]1)=[O:63])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 643495Benzyl piperazine-1-carboxylateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222827343-(4-{[(tert-Butoxycarbonyl)amino]methyl}phenyl)propanoic acid2×

Product 1

HCID 18752836HCID 18752836, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 11.4 ml of ethyldiisopropylamine in 20 ml of DMF is mixed successively with 3.11 g of 3-(4-tert-butyloxycarbonylaminomethylphenyl)propionic acid (starting material B4) and 4.64 g HBTU, with stirring. After ten minutes 2.45 g of 1-benzyloxycarbonylpiperazine are added and the mixture is stirred at RT for 5 h. The mixture is diluted with ethyl acetate and water. After phase separation, the organic phase is washed with 1N hydrochloric acid solution, 1N aqueous sodium hydroxide solution and water. After drying over magnesium sulfate, the organic solution is concentrated and the residue is chromatographed over silica gel (petrolether/ethyl acetate/acetone 4:5:1). Concentration of the pure fractions and drying in vacuo gives 3.91 g of the title compound as a yellowish powder. The mass spectrum shows the molecular peak MH+ at 481.8 Da.

Workup

  1. stirringthe mixture is stirred at RT for 5 h
  2. customAfter phase separation
  3. washthe organic phase is washed with 1N hydrochloric acid solution, 1N aqueous sodium hydroxide solution and water
  4. dry with materialAfter drying over magnesium sulfate
  5. concentrationthe organic solution is concentrated
  6. customthe residue is chromatographed over silica gel (petrolether/ethyl acetate/acetone 4:5:1)
  7. customConcentration of the pure fractions and drying in vacuo

Sources & evidence

ORD record
ord-602340549a2442e885733736a37cadfc
Source dataset
uspto-grants-2004_01
Patent number
US06673786B1

Reaction notes

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