Water → HCID 59323865, compound

HRID 1911546Notes

Reaction equation

HRID 1911546 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[N:8]=1)[CH2:3][OH:4].C([O-])([O-])=O.[K+].[K+].[N:23]#[C:24]Br.O>C1COCC1.C(OCC)(=O)C>[F:15][C:13]([F:16])([F:14])[C:9]1[N:8]=[C:7]([CH2:6][CH2:5][C@H:2]2[CH2:3][O:4][C:24]([NH2:23])=[N:1]2)[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 68715428HCID 68715428, compound

Product 1

HCID 59323865HCID 59323865, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of (S)-2-amino-4-(6-trifluoromethyl-pyridin-2-yl)-butan-1-ol (0.224 g, 0.96 mmol) and K2CO3 (0.198 g, 1.43 mmol) in THF (7 ml) under an argon atmosphere was added a solution of cyanogen bromide (0.152 g, 1.05 mmol) in THF (1 ml). The mixture was stirred for 18 hours, then water and ethyl acetate were added. The organic layer was washed with water, dried over MgSO4 and evaporated over Isolute® Flash-NH2 silicagel. Chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=90:10) yielded the title compound as off-white solid, (0.096 g, 39%); MS (ISP): 260.0 ((M+H)+.).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. customevaporated over Isolute® Flash-NH2 silicagel

Sources & evidence

ORD record
ord-97fde19d14464bf6b476454ab29355fe
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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