Trifluoroacetic acid → HCID 178421651, compound

HRID 853626Notes

Reaction equation

HRID 853626 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([O:21][Si](C(C)C)(C(C)C)C(C)C)=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:32][CH3:33])[C:9]=3[C:8]2(O)[CH3:34])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([OH:21])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:32][CH3:33])[C:9]=3[C:8]2=[CH2:34])=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 589289857-(4-Fluoro-benzyl)-6-hydroxy-5-methoxy-6-methyl-9-triisopropylsilanyloxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one

Product 1

HCID 178421651HCID 178421651, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 16 (10 mg, 0.019 mmol) in 3 mL of CH2Cl2 and TFA (30 μL, 0.389 mmol) was aged for 18 hours. Analysis of the reaction demonstrated complete conversion of starting materials to the product. The solvents were removed under reduced pressure. The residue was dissolved in EtOAc and precipitated with hexanes. The mother liquor was removed and the solid residue was washed with hexanes and subsequently with Et2O to yield the product 17 as a solid. 1H NMR (300 MHz, CDCl3) δ 3.97 (s, 3H), 4.99 (s, 2H), 5.04 (d, 1H, J=2 Hz), 5.63 (d, 1H, J=2 Hz), 6.90 (br s, 1H), 7.04 (t, 2H, J=8 Hz), 7.31 (dd, 2H, J=5, 8 Hz), 7.71 (dd, 1H, J=4, 8 Hz), 8.64 (dd, 1H, J=2, 9 Hz), 9.11 (d, 1H J=3Hz); 19F NMR (282.6 MHz, CDCl3) δ 62.1; EI MS (m/z) 351.5 [MH+], 383.3 [M+Na].

Workup

  1. customThe solvents were removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. customprecipitated with hexanes
  4. customThe mother liquor was removed
  5. washthe solid residue was washed with hexanes and subsequently with Et2O

Sources & evidence

ORD record
ord-5589f1be82974a6b821cb3f468db34af
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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