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

HRID 1968229Notes

Reaction equation

HRID 1968229 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) δ 1.50 (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-aa48ae7e3b6e48e09ddc5b00f185e462
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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