Trifluoroacetic acid → HCID 58641237, compound

HRID 1394934Notes

Reaction equation

HRID 1394934 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([O:16]C(C)(C)C)=O)[C:11]([CH3:27])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:10]=1.F[C:29](F)(F)C(O)=O.CCN(CC)CC.C(OC(=O)C)(=O)C>>[C:14]([N:12]1[CH2:13][C:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])=[CH:10][C:11]1([CH3:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:16])[CH3:29]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 71122379HCID 71122379, compound

Product 1

HCID 58641237HCID 58641237, compound

Procedure

To a flame-dried flask equipped with stir bar under nitrogen was charged 20-9 (14 mg, 38 μmol) and anhydrous CH2CL2 (1 mL). The resulting solution was treated with trifluoroacetic acid (0.2 mL) and stirred 1 hour at 25° C. Upon completion, the reaction was concentrated, diluted with toluene (5 mL) and again concentrated. The TFA salt was then suspended in CH2CL2 at 25° C., and treated successively with Et3N (50 μL, 380 μmol) and acetic anhydride (25 μL, 20 μmol). After 1 hour, the reaction was complete. The reaction was concentrated and flash column chromatography (SiO2, 0-50% EtOAc/hex gradient) provided 20-10 as a clear oil: 1H NMR (300 MHz, CDCl3) δ 7.36 (m, 5H), 7.03 (m, 3H), 6.22 (m, 1H), 4.82 (m, 2H), 2.15 and 2.05 (s, 3H, rotamers), 1.98 and 1.74 (s, 3H, rotamers); LRMS m/z (M+H) 314.0 found, 314.2 required.

Workup

  1. customTo a flame-dried flask equipped
  2. stirringstirred 1 hour at 25° C
  3. concentrationUpon completion, the reaction was concentrated
  4. additiondiluted with toluene (5 mL)
  5. concentrationagain concentrated
  6. customwas then suspended in CH2CL2 at 25° C.
  7. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-6bd63ab461264fa4ad4096b727bb27ef
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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