Trifluoroacetic acid → HCID 178489242, compound

HRID 2040107Notes

Reaction equation

HRID 2040107 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][NH:15][C:16]2[S:17][C:18](=[CH:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][C:31]=4[C:38]([F:41])([F:40])[F:39])=[C:25]([O:42][CH3:43])[CH:24]=3)[C:19](=[O:21])[N:20]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:43][O:42][C:25]1[CH:24]=[C:23]([CH:22]=[C:18]2[S:17][C:16]([NH:15][CH2:14][CH:10]3[O:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[N:20][C:19]2=[O:21])[CH:28]=[CH:27][C:26]=1[O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][C:31]=1[C:38]([F:40])([F:39])[F:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178489243HCID 178489243, compound

Product 1

HCID 178489242HCID 178489242, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

LC/MS (m/z) [M+1]+618.8 (calculated for C29H29F3N4O6S, 618.63). 2-({5-[4-(4-Cyano-2-trifluoromethyl-phenoxy)-3-methoxy-benzylidene]-4-oxo-4,5-dihydro-thiazol-2-ylamino}-methyl)-morpholine-4-carboxylic acid tert-butyl ester (0.1 g, 0.16 mmol) was dissolved in dry dichloromethane (6 mL). To the reaction mixture was then added at 0° C. trifluoroacetic acid (2 mL). The reaction mixture was stirred at 0° C. for 1 hour and then at room temperature for 30 minutes. The reaction mixture was then partitioned with saturated aqueous sodium bicarbonate and dichloromethane. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (6% ammonia 2.0 M methanol/dichloromethane) to yield the compound as a solid (0.052 g, 63%).

Workup

  1. waitat room temperature for 30 minutes
  2. customThe reaction mixture was then partitioned with saturated aqueous sodium bicarbonate and dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customto yield a crude oil
  8. customThe crude oil was purified via flash chromatography (6% ammonia 2.0 M methanol/dichloromethane)

Sources & evidence

ORD record
ord-923a3678257240689c14a56cf8bc160f
Source dataset
uspto-grants-2013_11
Patent number
US08580832B2

Reaction notes

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