Dimethylformamide → (s)-[1-(2-Amino-4-methyl-pentyl)-piperidin-4-yl]-(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amine

HRID 2299900Notes

Reaction equation

HRID 2299900 reaction equation
O.C([NH:9][C@H:10]([C:15](O)=O)[CH2:11][CH:12]([CH3:14])[CH3:13])(OC(C)(C)C)=O.[CH3:18][CH2:19][N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22].Cl.[CH3:28][O:29]NC.CN(C(ON1N=N[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[N:57]([CH:59]=O)[CH3:58]>CCOC(C)=O>[NH2:9][C@@H:10]([CH2:11][CH:12]([CH3:13])[CH3:14])[CH2:15][N:57]1[CH2:58][CH2:23][CH:21]([N:20]([C:24]2[CH:26]=[CH:15][C:10]([O:29][CH2:28][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[CH:11][CH:25]=2)[CH2:19][CH:18]=[C:12]([CH3:14])[CH3:13])[CH2:22][CH2:59]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12373896N-Boc-L-Leucine Hydrate

Product 1

HCID 11744448(s)-[1-(2-Amino-4-methyl-pentyl)-piperidin-4-yl]-(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Boc-L-leucine hydrate (10.0 g, 40.0 mmol) was dissolved in DMF (200 mL), treated with Hunig's base (21 mL, 120 mmol), O,N-dimethylhydroxylamine hydrochloride salt (3.9 g, 40 mmol), and HBTU (15.16 g, 40 mmol), and stirred for 1 hour. The reaction was diluted with EtOAc (1 L), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated to give 12.2 g of the desired product as a pale oil.

Workup

  1. washwashed with saturated bicarbonate solution and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d52eee3d6b0f4ad786deacc746a61db0
Source dataset
uspto-grants-2002_12
Patent number
US06495715B2

Reaction notes

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