Trifluoroacetic acid → N-((R)-1-(4-Fluorophenyl)-2-hydroxyethyl)-4-((S)-morpholin-2-yl)benzamide

HRID 710257Notes

Reaction equation

HRID 710257 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[O:25][CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]3)=[CH:16][CH:15]=2)=[O:13])[CH2:9][OH:10])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:11][C:12](=[O:13])[C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[O:25][CH2:24][CH2:23][NH:22][CH2:21]3)=[CH:16][CH:15]=2)[CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89689438HCID 89689438, compound

Product 1

HCID 89689472N-((R)-1-(4-Fluorophenyl)-2-hydroxyethyl)-4-((S)-morpholin-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-butyl 2-(4-((R)-1-(4-fluorophenyl)-2-hydroxyethylcarbamoyl)phenyl)morpholine-4-carboxylate (44 mg, 0.099 mmol) was dissolved in dichloromethane (0.3 ml) and trifluoracetic acid (447 mg, 0.3 ml, 3.92 mmol) was added. The reaction mixture was stirred at room temperature for 60 min. The solvent and excess of trifluoracetic acid were evaporated. The residue was dissolved in dichloromethane (3 ml) and extracted with odium bicarbonate saturated solution (2 ml). The organic layer was dried over MgSO4 and evaporated. The crude product was directly used for the next step.

Workup

  1. customThe solvent and excess of trifluoracetic acid were evaporated
  2. dissolutionThe residue was dissolved in dichloromethane (3 ml)
  3. extractionextracted with odium bicarbonate saturated solution (2 ml)
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-8e991b8a49ac4ae1b636bb15359c4856
Source dataset
uspto-grants-2015_11
Patent number
US09181230B2

Reaction notes

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