Cyclopentylamine → HCID 68319152, compound

HRID 1627116Notes

Reaction equation

HRID 1627116 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C@H:13]([CH3:16])[CH2:14][CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=N[C:27]2[CH:28]=[CH:29][CH:30]=[N:31][C:26]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CCCC1.CCN(CC)CC>C(Cl)Cl>[CH:26]1([NH:31][C:10](=[O:12])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C@H:13]([CH3:16])[CH2:14][CH3:15])[CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

6

Reactant 4

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 6992552HCID 6992552, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68319152HCID 68319152, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2R,3R)-2-(tert-butoxycarbonylamino)-3-methylpentanoic acid (0.5 g, 2.162 mmol, HATU (0.986 g, 2.59 mmol) and cyclopentanamine (0.427 mL, 4.32 mmol) in DCM (10 mL) was added Et3N (0.603 mL, 4.32 mmol). The reaction mixture was stirred at room temperature for 5 h and then washed with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4 and concentrated. Purification by silica column chromatography (MeOH/DCM, 0-10%) afforded the title compound (0.56 g, 87%). 1H NMR (400 MHz, CDCl3) δ 0.82-0.89 (m, 3 H) 0.92 (t, J=7.45 Hz, 3 H) 1.32-1.41 (m, 6 H) 1.44 (s, 9 H) 1.55-1.77 (m, 3 H) 1.84-2.04 (m, 2 H) 2.99 (d, J=4.29 Hz, 1 H) 3.96 (dd, J=8.72, 5.43 Hz, 1 H) 4.21 (dt, J=13.89, 6.95 Hz, 1 H) 5.02 (br. s., 1 H) 5.93 (br. s., 1 H).

Workup

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

Sources & evidence

ORD record
ord-3570bf2178fa4e63bdc29ca81b40e465
Source dataset
uspto-grants-2014_07
Patent number
US08785429B2

Reaction notes

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