Leucic acid, L- → (s)-1-{4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-2-hydroxy-4-methyl-pentan-1-one

HRID 1069190Notes

Reaction equation

HRID 1069190 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][CH:28]([CH2:30][C@H:31]([OH:35])[C:32](O)=[O:33])[CH3:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH:16]2[CH2:21][CH2:20][N:19]([C:32](=[O:33])[C@@H:31]([OH:35])[CH2:30][CH:28]([CH3:29])[CH3:27])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 83697Leucic acid, L-HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10641624(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-piperidin-4-yl-amine

Product 1

HCID 54017394(s)-1-{4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-2-hydroxy-4-methyl-pentan-1-oneYield 49.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-piperidin-4-yl-amine (Ic) (0.89 g, 2.54 mmol) was dissolved in DMF (17 mL) and treated with N,N-diisopropyletbylamine (1.77 mL, 10.17 mmol), L-2-hydroxyisocaproic acid (0.34 g, 2.54 mmol), and HBTU (0.96 g, 2.54 mmol). The reaction was stirred for 3 hours, then diluted with EtOAc (200 mL), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel eluting with 4% MeOH/CH2Cl2 to give 0.58 g (49%) of the desired product.

Workup

  1. washwashed with saturated bicarbonate solution and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel eluting with 4% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-af59c1838bcc41a2ab64d3badd4e6505
Source dataset
uspto-grants-2001_06
Patent number
US06251919B1

Reaction notes

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