2-Methylbutylamine → HCID 59620930, compound

HRID 1099023Notes

Reaction equation

HRID 1099023 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:17][CH:18]([CH2:21][CH3:22])[CH2:19][NH2:20].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC#N>[CH3:6][CH:4]([CH3:5])[CH2:3][C@H:2]([NH:1][C:10](=[O:11])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:7]([NH:20][CH2:19][CH:18]([CH3:17])[CH2:21][CH3:22])=[O:9]

Participants

6

Reactant 4

HCID 72832-MethylbutylamineHCID 81531DiisopropylethylamineHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 59620930HCID 59620930, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of Boc-Leu-OH (61.3 mg, 0.26 mmol), 2-methylbutylamine (0.046 ml, 0.40 mmol) and 3 ml of MeCN in a round bottom flask equipped with a magnetic stirring bar was added DIEA (0.092 ml, 0.53 mmol) followed by HBTU (120 mg, 0.32 mmol). The reaction mixture was stirred at room temperature for 16 hours at which point TLC analysis showed that the reaction was complete. The mixture was concentrated under reduced pressure. 10 ml of DCM was added and this mixture was washed with water (×3), citric acid (1M, ×3), and brine (×1), dried over Na2SO4 and concentrated under reduced pressure. The crude 1H NMR showed that the product was pure enough to carry over to the next step. 1H NMR (CDCl3, 300 MHz): δ 6.75 (b, 1H), 5.21 (b, 1H), 4.18 (b, 1H), 3.17 (m, 2H), 1.77-1.07 (m, 16H), 0.98 (m, 12H) ppm; 13C NMR (CDCl3, 75 MHz): δ 172.9, 156.0, 53.3, 45.1, 41.4, 35.0, 28.4, 27.1, 27.1, 27.0, 24.9, 23.0, 22.3, 17.2, 17.1, 11.4, 11.3 ppm. HRMS (ESI+) [M+H]+ calcd. for C16H33N2O3 301.2485, found 301.2489.

Workup

  1. customequipped with a magnetic stirring bar
  2. concentrationThe mixture was concentrated under reduced pressure
  3. addition10 ml of DCM was added
  4. washthis mixture was washed with water (×3), citric acid (1M, ×3), and brine (×1)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4de136154d8344c4a799f3a9b4c83834
Source dataset
uspto-grants-2012_03
Patent number
US08143375B2

Reaction notes

Loading…