Allylamine → HCID 70008891, compound

HRID 1356525Notes

Reaction equation

HRID 1356525 reaction equation
[C:1]([NH:11][C@H:12]([C:17]([OH:19])=O)[CH2:13][CH:14]([CH3:16])[CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN1CCOCC1.[CH2:27]([NH2:30])[CH:28]=[CH2:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[C:1]([NH:11][C@H:12]([C:17]([NH:30][CH:27]=[CH:28][CH3:29])=[O:19])[CH2:13][CH:14]([CH3:15])[CH3:16])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

7

Reactant 4

HCID 7853AllylamineHCID 79724-MethylmorpholineHCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 70008891HCID 70008891, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-Cbz-leucine (3.0 g, 11.3 mmol) was dissolved in DMF (50 ml), then NMM (1.3 g, 12.4 mmol) was added, followed by allyl amine (0.65 g, 0.85 mmol), and HBTU (4.3 g, 11.3 mmol) and the reaction was stirred overnight at RT. The reaction was diluted with water, extracted with EtOAc, dried with magnesium sulfate, filtered, concentrated, and chromatographed (silica gel, 40% EtOAc:hexanes): MS(ES) M+H+=305.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed (silica gel, 40% EtOAc:hexanes)

Sources & evidence

ORD record
ord-d534ee9a21ef47dea9b7db36c5c27d86
Source dataset
uspto-grants-2003_07
Patent number
US06586466B2

Reaction notes

Loading…