Pyridine → HCID 86706344, compound

HRID 1396866Notes

Reaction equation

HRID 1396866 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[F:25]C1N=C(F)N=C(F)N=1>C(Cl)Cl>[CH:1]1([CH2:6][C@@H:7]([C:8]([F:25])=[O:9])[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 9816539(R)-4-(tert-Butoxy)-2-(cyclopentylmethyl)-4-oxobutanoic acid

Product 1

HCID 86706344HCID 86706344, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2R)-2-(cyclopentylmethyl)-4-[(1,1-dimethylethyl)oxy]-4-oxobutanoic acid (Tetrahedron, 2001, 57(36), 7675-7683) (4.0 g, 15.60 mmol) in DCM was added pyridine (1.38 ml, 17.2 mmol) and a solution of 2,4,6-trifluoro-1,3,5-triazine (2.3 g, 17.2 mmol) in DCM (10 mL). The reaction was stirred at room temperature for 2 h. The solution was then washed with citric acid (20 mL×2) and brine (20 mL), then concentrated to provide the crude product, 1,1-dimethylethyl (3R)-3-(cyclopentylmethyl)-4-fluoro-4-oxobutanoate, as a yellow oil (3.8 g, 57% yield), which was used directly in the next step. MS: 257 ([M−H]+).

Workup

  1. washThe solution was then washed with citric acid (20 mL×2) and brine (20 mL)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-af3788185baa4582b51c72a1b7b32d4b
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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