Trifluoroacetic acid → HCID 10255457, compound

HRID 853651Notes

Reaction equation

HRID 853651 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][NH:10][C:11]([C:13]1[C:14]2[CH:15]=[CH:16][CH:17]=[N:18][C:19]=2[C:20]([O:35]C(C2C=CC=CC=2)C2C=CC=CC=2)=[C:21]2[C:25](=[O:26])[N:24]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[CH2:23][C:22]=12)=[O:12])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:6]([O:5][P:4]([CH2:9][NH:10][C:11]([C:13]1[C:14]2[CH:15]=[CH:16][CH:17]=[N:18][C:19]=2[C:20]([OH:35])=[C:21]2[C:25](=[O:26])[N:24]([CH2:27][C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[CH2:23][C:22]=12)=[O:12])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86593995HCID 86593995, compound

Product 1

HCID 10255457HCID 10255457, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 216 (20 mg, 0.030 mmol) in 0.30 mL of CH2Cl2 was stirred with TFA (231 μL, 3.00 mmol) and TES (479 μL, 3.00 mmol) for 30 minutes when the starting materials were completely consumed as judged by TLC and LCMS. The reaction was worked up by removal of the solvent in vacuo and crystallizing the product from EtOAc-Hex to provide 10 mg (66%) of ({[7-(4-Fluoro-benzyl)-9-hydroxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinoline-5-carbonyl]-amino}-methyl)-phosphonic acid diethyl ester 217 as a yellow solid. 1H NMR (300 MHz, CD3OD) δ 1.32 (t, 6H, J=7 Hz), 3.96 (d, 2H, J=12 Hz), 4.16 (septet, 4H, J=7 Hz), 4.56 (s, 2H), 4.79 (s, 2H), 7.10 (t, 2H, J=9 Hz), 7.39 (dd, 2H, J=9 Hz), 7.76 (br s, 1H), 8.66 (d, 1H, J=8 Hz), 8.95 (br s, 1H); 31P (121.4 MHz, CD3OD) δ 23.2; 19F NMR (282.6 MHz, CD3OD) δ −76.2, 59.9; MS (m/z) 502.5 [M+H]+, 1003.0 [2M]+, 1025.1 [2M+Na]+.

Workup

  1. customwere completely consumed
  2. customThe reaction was worked up by removal of the solvent in vacuo
  3. customcrystallizing the product from EtOAc-Hex

Sources & evidence

ORD record
ord-87bb3bbca23a44c799f6c2993f084618
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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