Trifluoroacetic acid → HCID 25218471, compound

HRID 2196530Notes

Reaction equation

HRID 2196530 reaction equation
[CH3:1][O:2][C:3]1[CH:41]=[CH:40][CH:39]=[CH:38][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[N:13]([C:14]2[N:19]=[C:18]([CH2:20][NH:21][C:22](=[O:33])[C@@H:23]([NH:25]C(=O)OC(C)(C)C)[CH3:24])[CH:17]=[CH:16][CH:15]=2)[N:12]=[C:11]([C:34]([F:37])([F:36])[F:35])[CH:10]=1)=[O:8].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:25][C@@H:23]([CH3:24])[C:22]([NH:21][CH2:20][C:18]1[N:19]=[C:14]([N:13]2[C:9]([C:7]([NH:6][CH2:5][C:4]3[CH:38]=[CH:39][CH:40]=[CH:41][C:3]=3[O:2][CH3:1])=[O:8])=[CH:10][C:11]([C:34]([F:35])([F:37])[F:36])=[N:12]2)[CH:15]=[CH:16][CH:17]=1)=[O:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59843206HCID 59843206, compound

Product 1

HCID 25218471HCID 25218471, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
21 °C

Procedure

To a stirred solution of 50 (28 mg, 0.049 mmol) in CH2Cl2 (1 mL) was added trifluoroacetic acid (0.056 mL, 0.728 mmol). The resulting solution was allowed to stir at 21° C. for 2 h and evaporated to dryness. Water was added and the precipitate was removed by filtration. The aqueous phase was then lyophilized. The title product 51 (16.1 mg, 56.1% yield) was isolated as a white solid. 1H NMR: (CD3OD) o(ppm): 7.99 (t, 1H, J=8.0 Hz), 7.73 (d, 1H, J=8.0 Hz), 7.38 (d, 1H, J=7.6 Hz), 7.26 (d, 2H, J=7.6 Hz), 7.09 (s, 1H), 6.96 (d, 1H, J=7.6 Hz), 6.91 (t, 1H, J=7.6 Hz), 4.51 (dd, 2H, J=15.2, 23.6 Hz), 4.32 (dd, 2H, J=16, 54.4 Hz), 3.95 (q, 1H, J=7.2 Hz), 3.80 (s, 3H), 1.51 (d, 3H, J=6.8 Hz). LRMS (ESI): calc. 476.5; found 477.5 (MH)+.

Workup

  1. customevaporated to dryness
  2. additionWater was added
  3. customthe precipitate was removed by filtration

Sources & evidence

ORD record
ord-45090622379a4687bc4580872b87d5b2
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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