Trifluoroacetic acid → HCID 44199303, compound

HRID 1842169Notes

Reaction equation

HRID 1842169 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:10]1[CH:11]=[CH:12][C:13]([C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([F:44])=[C:23]([C@:25]34[CH2:33][C@H:32]([O:34][CH3:35])[CH2:31][C@H:30]3[CH2:29][S:28][C:27]([NH:36]C(=O)OC(C)(C)C)=[N:26]4)[CH:24]=2)=[O:17])=[N:14][CH:15]=1)#[N:9].C(=O)(O)[O-].[Na+]>ClCCl>[NH2:36][C:27]1[S:28][CH2:29][C@@H:30]2[CH2:31][C@@H:32]([O:34][CH3:35])[CH2:33][C@:25]2([C:23]2[CH:24]=[C:19]([NH:18][C:16]([C:13]3[CH:12]=[CH:11][C:10]([C:8]#[N:9])=[CH:15][N:14]=3)=[O:17])[CH:20]=[CH:21][C:22]=2[F:44])[N:26]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57827508HCID 57827508, compound

Product 1

HCID 44199303HCID 44199303, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.0 mL) was added to a solution of tert-butyl ((4aR*,6R*,7aS*)-7a-{5-[(5-cyanopyridine-2-carbonyl)amino]-2-fluorophenyl}-6-methoxy-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl)carbamate (29 mg) in dichloromethane (2 mL), and the reaction solution was stirred at room temperature for one hour. The reaction solution was poured into a saturated sodium bicarbonate solution, followed by extraction with ethyl acetate. The extract was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The crude product was purified by NH-silica gel column chromatography to obtain the title compound (12 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe crude product was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-6d67193b67e04b34a88d2c01c98a0070
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

Loading…