Diisopropylethylamine → HCID 57589913, compound

HRID 1783392Notes

Reaction equation

HRID 1783392 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH:9]([C:13]([OH:15])=O)[CH2:10][CH:11]=[CH2:12])=[O:7])([CH3:4])[CH3:3].C1CCC(NC2CCCCC2)CC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:60]([NH:63][CH2:64][C:65]1[CH:70]=[CH:69][C:68]([O:71][CH3:72])=[CH:67][C:66]=1[O:73][CH3:74])[CH:61]=[CH2:62]>CN(C)C=O>[C:2]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([C:13](=[O:15])[N:63]([CH2:60][CH:61]=[CH2:62])[CH2:64][C:65]1[CH:70]=[CH:69][C:68]([O:71][CH3:72])=[CH:67][C:66]=1[O:73][CH3:74])[CH2:10][CH:11]=[CH2:12])([CH3:1])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4722371HCID 4722371, compoundHCID 11099301O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 53395397Boc-L-allylglycine . DCHA

Product 1

HCID 57589913HCID 57589913, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(R)-N-Boc-allylglycine (2.3 g, 9.9 mmol) was dissolved in dimethylformamide (20 ml) and activated with the coupling reagent TATU (3.5 g, 10.9 mmol) and Hünig's base (3.8 ml, 21.9 mmol) for 2 min. Allyl-(2,4-dimethoxy-benzyl)-amine (2.1 g, 9.9 mmol) dissolved in dimethylformamide (20 ml) was added to the chilled (ice-water bath) reaction mixture and the stirring was continued overnight. The solvent was evaporated and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution, 1 M KHSO4 solution, brine, dried (MgSO4.2H2O), filtered and concentrated under reduce pressure and purified over silica gel (ethyl acetate/n-heptane 1:4): colorless gum 2.6 g (62%);

Workup

  1. additionwas added to the
  2. temperaturechilled
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with saturated NaHCO3 solution, 1 M KHSO4 solution, brine
  6. dry with materialdried (MgSO4.2H2O)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified over silica gel (ethyl acetate/n-heptane 1:4)

Sources & evidence

ORD record
ord-8c66eddc371c43c7a53c3ee05b304da1
Source dataset
uspto-grants-2009_03
Patent number
US07501406B2

Reaction notes

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