Allylamine → HCID 70008891, compound

HRID 1977487Notes

Reaction equation

HRID 1977487 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-021a8954d09143ee9d80e8248c939425
Source dataset
uspto-grants-2001_05
Patent number
US06232342B1

Reaction notes

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