Cyanogen Bromide → (2S)-2-(5-Amino-1,3,4-oxadiazol-2-yl)-1,1,1-trifluoropropan-2-ol

HRID 1988188Notes

Reaction equation

HRID 1988188 reaction equation
[F:1][C:2]([F:11])([F:10])[C@:3]([OH:9])([CH3:8])[C:4]([NH:6][NH2:7])=[O:5].[N:12]#[C:13]Br.C(=O)(O)[O-].[K+]>O>[NH2:12][C:13]1[O:5][C:4]([C@@:3]([OH:9])([CH3:8])[C:2]([F:10])([F:11])[F:1])=[N:6][N:7]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 516893Potassium BicarbonateHCID 57729253(2S)-3,3,3-Trifluoro-2-hydroxy-2-methylpropanohydrazide

Product 1

HCID 57729248(2S)-2-(5-Amino-1,3,4-oxadiazol-2-yl)-1,1,1-trifluoropropan-2-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (2S)-3,3,3-trifluoro-2-hydroxy-2-methylpropanohydrazide (3.0 g, 17.5 mmol) in water (17 ml) was added cyanogen bromide (1.87 g, 17.7 mmol) and potassium bicarbonate (1.82 g, 18.1 mmol). The reaction mixture was stirred 30 min at rt until a white precipitate was formed. The precipitate was filtered and washed with water followed by a mixture of ether-hexanes (1:1) to afford the title compound. 1H NMR (400 MHz, acetone-d6): δ 6.57 (bs, 2H), 6.20 (bs, 1H), 1.80 (s, 3H).

Workup

  1. customwas formed
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. additionfollowed by a mixture of ether-hexanes (1:1)

Sources & evidence

ORD record
ord-30aba372cc8a43859213f6bf39fa244e
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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