Cyclopentylamine → (R)-tert-butyl 3-cyano-1-(cyclopentylamino)-1-oxopropan-2-ylcarbamate

HRID 1627133Notes

Reaction equation

HRID 1627133 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][C:14]#[N:15])[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>[C:14]([CH2:13][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]([NH:30][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29]1)=[O:12])#[N:15]

Participants

6

Reactant 4

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 7019662Boc-beta-cyano-D-alanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67225088(R)-tert-butyl 3-cyano-1-(cyclopentylamino)-1-oxopropan-2-ylcarbamateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (R)-2-(tert-butoxycarbonylamino)-3-cyanopropanoic acid (0.5 g, 2.334 mmol), HATU (0.986 g, 2.59 mmol) and cyclopentanamine (0.461 mL, 4.67 mmol) in DCM (10 mL) was added Et3N (0.651 mL, 4.67 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 (0.61 g, 93%). 1H NMR (400 MHz, CD3OD) δ1.50 (s, 9 H) 1.57-1.73 (m, 4 H) 1.79-1.87 (m, 3 H) 1.89-2.02 (m, 1 H) 2.05-2.19 (m, 3 H) 2.76-2.95 (m, 1 H) 3.87 (t, J=7.07 Hz, 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-6ac2efabe51d4cb4ace607b430a2898e
Source dataset
uspto-grants-2014_07
Patent number
US08785429B2

Reaction notes

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