Trifluoroacetic acid → HCID 57948959, compound

HRID 1992278Notes

Reaction equation

HRID 1992278 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@:9]2([CH3:23])[CH2:14][CH2:13][S:12][C:11]([NH:15]C(=O)OC(C)(C)C)=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].FC(F)(F)C(O)=O>CO>[Br:1][C:2]1[CH:3]=[C:4]([C@:9]2([CH3:23])[CH2:14][CH2:13][S:12][C:11]([NH2:15])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68539143HCID 68539143, compound

Product 1

HCID 57948959HCID 57948959, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-tert-butyl 4-(3-bromo-4-fluorophenyl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-ylcarbamate (1.1 g, 2.7 mmoles) and methanol (10 mL) is added trifluoroacetic acid (10 mL). The reaction mixture is warmed to 60° C. After 15 h, the solvent is removed under reduced pressure. Water is added to the resulting residue and the mixture is made basic with saturated sodium bicarbonate. The basic aqueous phase is extracted with dichloromethane. The organic phase is separated, dried over sodium sulfate, filtered, and the solvent removed under reduced pressure to give the title compound (62% yield): MS (m/z): 303, 305 (M+1).

Workup

  1. customthe solvent is removed under reduced pressure
  2. additionWater is added to the resulting residue
  3. extractionThe basic aqueous phase is extracted with dichloromethane
  4. customThe organic phase is separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6b5b9a9dd65b485ebbfd38b5005f22c8
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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