Cyclopentylamine → HCID 28165435, compound

HRID 1968209Notes

Reaction equation

HRID 1968209 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=N[C:26]2[CH:27]=[CH:28][CH:29]=[N:30][C:25]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CCCC1.CCN(CC)CC>C(Cl)Cl>[CH:25]1([NH:30][C:10](=[O:12])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH:13]([CH3:15])[CH3:14])[CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 28165435HCID 28165435, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (R)-2-(tert-butoxycarbonylamino)-3-methylbutanoic acid (0.5 g, 2.301 mmol), HATU (1.05 g, 2.76 mmol) and cyclopentanamine (0.455 mL, 4.60 mmol) in DCM (20 mL) was added Et3N (0.642 mL, 4.60 mmol). The reaction mixture was stirred at room temperature for 5 h, washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, and concentrated. Purification by silica column chromatography (MeOH/DCM, 0-10%) afforded the title compound (0.61 g, 94%).

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification by silica column chromatography (MeOH/DCM, 0-10%)

Sources & evidence

ORD record
ord-a28f55bea32c4c36806bd1ca71b8d6d5
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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