Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → (2S)-2-[(5-bromopyridin-2-yl)(phenyl)methoxy]-N-(cyanomethyl)-4-methylpentanamide

HRID 1180437Notes

Reaction equation

HRID 1180437 reaction equation
ClC(Cl)(Cl)C(=N)O[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][N:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:22]([CH2:24][NH:25][C:26](=[O:33])[C@@H:27]([OH:32])[CH2:28][CH:29]([CH3:31])[CH3:30])#[N:23].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>ClCCCl>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([CH:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:32][C@@H:27]([CH2:28][CH:29]([CH3:30])[CH3:31])[C:26]([NH:25][CH2:24][C:22]#[N:23])=[O:33])=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 69476307(5-Bromopyridin-2-yl)(phenyl)methyl 2,2,2-trichloroethanimidoateHCID 86605382HCID 86605382, compound

Product 1

HCID 86605403(2S)-2-[(5-bromopyridin-2-yl)(phenyl)methoxy]-N-(cyanomethyl)-4-methylpentanamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (5-bromopyridin-2-yl)(phenyl)methyl 2,2,2-trichloroethanimidoate from example 53 step 2 (2 g, 4.9 mmol) in 1,2-dichloroethane (50 mL) was added (2S)-N-(cyanomethyl)-2-hydroxy-4-methylpentanamide (830 mg, 4.9 mmol, 1 eg) and camphor sulfonic acid (114 mg, 0.49 mmol, 0.10 eg). The suspension was heated to reflux for 18 hours, then concentrated to dryness. Residue was chromatographed with 25% EtOAc/hexane to yield the title compound.

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 18 hours
  3. concentrationconcentrated to dryness
  4. customResidue was chromatographed with 25% EtOAc/hexane

Sources & evidence

ORD record
ord-df67163a30ca4b48ae14ad5ef606111b
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

Loading…