Trifluoroacetic acid → HCID 86638090, compound

HRID 1920768Notes

Reaction equation

ClCC([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]([C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:12]2)=[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+]>C(Cl)Cl>[Cl:21][CH2:33][C:34]([O:36][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]([C:15](=[O:20])[C:16]([F:17])([F:18])[F:19])[CH2:12]2)=[CH:7][CH:6]=1)=[O:35]

Participants

Conditions

Temperature: 0 °C

Procedure

Compound (5) (8.4 g, 27 mmol) was dissolved in anhydrous CH2Cl2 (58 ml) and 3-chloroperoxybenzoic acid (mCPBA) (12.3 g) was added in one portion. The suspension was cooled to 0° C., and trifluoroacetic acid (2.0 ml) was added dropwise over 5-10 min. The reaction flask was protected from light, and the mixture was stirred for 3-5 days at room temperature, poured onto water (100 ml), and neutralized with ammonium hydroxide solution. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (60 ml). After purification on a silica gel column (n-hexane/EtOAc=2:1) the title compound was obtained as a yellow oil (6) (4.24 g, 48%). TLC Rf=0.5 (n-hexane/EtOAc=3:1). 1H NMR (300 MHz, CDCl3) (NMR, Varian Gemini): δ 7.20 (t, J=7 Hz, 1H, Aryl H), 7.01-6.93 (m, 2H, 2H, Aryl Ha), 4.75 (s, 2H, Ph-CH2—N), 4.33 (s, 2H, CO—CH2—), 3.90-3.82 (m, 2H, M—CH2—), 2.97-2.92 (m, 2H, Ph-CH2—). Fast Atom Bombardment Mass Spectrometry (FABMS) m/z: 322 (M+1) (C13H11NO3ClF3).

Workup

additionpoured onto water (100 ml)
customThe layers were separated
extractionthe aqueous layer was extracted with CH2Cl2 (60 ml)
customAfter purification on a silica gel column (n-hexane/EtOAc=2:1) the title compound

Sources & evidence

ORD record: ord-c281bc62e39e4ccf90118d07f85d42da
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173648B2

Reaction notes

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