Ethyl Acetate → HCID 25263632, compound

HRID 1094333Notes

Reaction equation

HRID 1094333 reaction equation
[NH:1]1[C:5]([C@@H:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[S:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=3)=[CH:10][CH:9]=2)[CH3:7])=[N:4][CH:3]=[N:2]1.CC[O:26]C(C)=O>C1C=C(Cl)C=C(C(OO)=O)C=1>[F:22][C:20]([F:23])([F:21])[C:18]1[N:19]=[C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([C@H:6]([C:5]3[N:1]([OH:26])[N:2]=[CH:3][N:4]=3)[CH3:7])=[CH:9][CH:10]=2)[S:16][CH:17]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86645986HCID 86645986, compound

Product 1

HCID 25263632HCID 25263632, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 70297m-Chloroperbenzoic acidSolvent

Procedure

To a solution of intermediate 15b (0.21 g, 0.62 mmol) in EtOAc (5 ml), m-CPBA was added (0.17 g, 0.97 mmol) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was washed with water (2×10 ml) and anhydrous Na2SO4 and evaporated under vacuum to give a crude that, after purification by flash chromatography, afforded the pure 5-[(1R)-1-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)ethyl]-1H-1,2,4-triazol-1-ol (15) as a white solid (67%). [α]D=−35 (c=0.82; CH3OH); 1H-NMR (CD3OD): δ 9.40 (bs, 1H, NH); 7.55 (d, 1H, J=2.5 Hz); 7.40 (d, 2H, J=7 Hz); 7.35 (d, 2H, J=7 Hz); 7.15 (s, 1H), 6.25 (d, 1H, J=2.4 Hz); 3.80 (q, 1H, J=7 Hz); 1.60 (d, 3H, J=7 Hz).

Workup

  1. washThe reaction mixture was washed with water (2×10 ml) and anhydrous Na2SO4
  2. customevaporated under vacuum
  3. customto give a crude that,
  4. customafter purification by flash chromatography

Sources & evidence

ORD record
ord-69f1b347659d478680965713adc2a1d4
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

Loading…