Trifluoroacetic acid → HCID 86757494, compound

HRID 1349922Notes

Reaction equation

ClCC([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C@H:11]2[NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])=[CH:7][CH:6]=1)=O.[Cl:21]C1C=C(C=CC=1)C(OO)=O.F[C:33](F)(F)[C:34]([OH:36])=[O:35].[OH-].[NH4+]>ClCCl.O>[Cl:21][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C@:11]2([O:36][C:34]([CH3:33])=[O:35])[NH:14][C:15](=[O:20])[C:16]([F:17])([F:18])[F:19])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6-Choroacetyl-N-trifluoroacetyl-(R)-1-aminoindan (30.57 g, 0.1 mol) was dissolved in anhydrous dichloromethane (210 ml) and 3-chloroperoxybenzoic acid (70%, 44.87 g, 0.26 mol) was added all at once. The suspension was cooled to 0° C. and trifluoroacetic acid (11.4 g, 0.1 mol) was added dropwise for 5-10 minutes. The reaction flask was protected from light and the mixture was stirred for 3-5 days at room temperature. The reaction mixture was poured into water (300 ml.). The mixture was neutralized with ammonium hydroxide solution. The layers were separated. The aqueous layer was extracted with dichloromethane (200 ml). The combined organic layers were dried (Na2SO4) and the solvent was removed under reduced pressure to give a solid, which was recrystallized from ethanol to give 15 g (48%) of a white solid mp: 169-170° C.

Workup

customThe layers were separated
extractionThe aqueous layer was extracted with dichloromethane (200 ml)
dry with materialThe combined organic layers were dried (Na2SO4)
customthe solvent was removed under reduced pressure
customto give a solid, which
customwas recrystallized from ethanol

Sources & evidence

ORD record: ord-e10faa7bb3ff451b8a9252ddb3af5e83
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE039616E1

Reaction notes

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