Pyridine → HCID 45092039, compound

HRID 1246206Notes

Reaction equation

HRID 1246206 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH3:14])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[F:21]C1N=C(F)N=C(F)N=1>C(Cl)Cl>[F:21][C:10]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 2755934(S)-2-((tert)-Butoxycarbonyl)amino)butanoic acid

Product 1

HCID 45092039HCID 45092039, compoundYield 111.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-2-(Tert-butoxycarbonylamino)butyric acid (0.010 mol) dissolved in DCM (25 ml) was placed in a cooling bath at −10° C. Pyridine (0.010 mol) was added, followed by 2,4,6-trifluoro-1,3,5-triazine (0.0345 mol). The mixture was stirred under nitrogen. After one hour, ice cold water (75 ml) was added. More DCM (45 ml) was added, and the mixture was shaken. The organic phase was separated, washed with ice cold water again (100 ml), then the organic phase dried, filtered, and concentrated to yield 2.29 g of (S)-1,1-dimethylethyl [1-(fluorocarbonyl)propyl]-carbamate (intermediate 25).

Workup

  1. customwas placed in a cooling bath at −10° C
  2. stirringthe mixture was shaken
  3. customThe organic phase was separated
  4. washwashed with ice cold water again (100 ml)
  5. customthe organic phase dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b34a80d2c9a34178ba71ab3cf2c1fdea
Source dataset
uspto-grants-2006_10
Patent number
US07125891B2

Reaction notes

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