Trifluoromethanesulfonic acid → HCID 19390780, compound

HRID 1756706Notes

Reaction equation

HRID 1756706 reaction equation
C(OC([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:35]([CH3:37])[CH3:36])[C:24](=[O:34])[C:25]([F:33])([F:32])[C:26](=[O:31])[NH:27][CH2:28][CH2:29][CH3:30])=[O:21])[C:15]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[N:14][CH:13]=1)=O)C1C=CC=CC=1.FC(F)(F)S(O)(=O)=O>ClCCl.C1(OC)C=CC=CC=1>[NH2:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:35]([CH3:37])[CH3:36])[C:24](=[O:34])[C:25]([F:33])([F:32])[C:26](=[O:31])[NH:27][CH2:28][CH2:29][CH3:30])=[O:21])[C:15]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[N:14][CH:13]=1

Participants

5

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 19390812HCID 19390812, compound

Product 1

HCID 19390780HCID 19390780, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

A suspension of the product from Example 1 (0.29 g) in dichloromethane (4 mL) and anisole (0.17 mL) was cooled in an ice-water bath. Trifluoromethanesulfonic acid (0.23 mL) was added to the mixture dropwise. The dark colored, gummy reaction mixture was allowed to warm to room temperature. After 30 minutes, the reaction mixture was cooled in an ice-water bath and was quenched with saturated sodium bicarbonate. The mixture was extracted with ethyl acetate and the extracts were washed (saturated sodium bicarbonate, brine), dried, and evaporated. The crude product was purified by trituration with ether to yield the title compound as a white solid (0.16 g); TLC: Rf =0.19, methanol:dichloromethane (5:95); NMR: 0.75 (d,3), 0.82 (t,3), 0.86 (d,3), 1.40-1.50 (m,2), 2.20-2.30 (m,1), 3.08 (q,2), 4.50 (q,2), 4.82 (dd,1), 5.17 (broad s, 2); MS: m/z=464 (M+1).

Workup

  1. temperaturewas cooled in an ice-water bath
  2. temperaturethe reaction mixture was cooled in an ice-water bath
  3. customwas quenched with saturated sodium bicarbonate
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe extracts were washed (saturated sodium bicarbonate, brine)
  6. customdried
  7. customevaporated
  8. customThe crude product was purified by trituration with ether

Sources & evidence

ORD record
ord-ddd220e98f184ff893ea85078178718b
Source dataset
uspto-grants-1995_08
Patent number
US05441960

Reaction notes

Loading…