Trifluoroacetic acid → HCID 90016379, compound

HRID 920147Notes

Reaction equation

HRID 920147 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:33])=[C:6]([C@:8]([N:15](CC2C=CC(OC)=CC=2OC)[C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])([CH3:14])[CH2:9][S:10][CH2:11][C:12]#[N:13])[CH:7]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:33])=[C:6]([C@:8]([NH:15][C:16](=[O:21])[C:17]([F:18])([F:20])[F:19])([CH3:14])[CH2:9][S:10][CH2:11][C:12]#[N:13])[CH:7]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 90016246HCID 90016246, compound

Product 1

HCID 90016379HCID 90016379, compoundYield 65.3%

Conditions

Temperature
23 °C

Procedure

A mixture of (R)—N-(2-(5-bromo-2-fluorophenyl)-1-(cyanomethylthio)propan-2-yl)-N-(2,4-dimethoxybenzyl)-2,2,2-trifluoroacetamide (5.9 g, 10.7 mmol, Eq: 1.00) and trifluoroacetic acid (73.5 g, 49.6 ml, 644 mmol, Eq: 60) was stirred at 23° C. for 16 hours resulting in a dark red solution. Poured into sat. NaHCO3-sol. and extracted twice with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by silica gel column chromatography 0 to 50% ethyl acetate in heptane to give the (R)—N-(2-(5-bromo-2-fluorophenyl)-1-(cyanomethylthio)propan-2-yl)-2,2,2-trifluoroacetamide (3.1 g, 6.99 mmol, 65.1% yield) as a light brown oil. MS (ISN): m/z=396.7 [M−H]− and 399.0 [M+2H]−.

Workup

  1. customresulting in a dark red solution
  2. extractionand extracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography 0 to 50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-49356e8325dc4e8caa7be3bc9f14a5a4
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

Loading…