Trifluoroacetic acid → HCID 11660921, compound

HRID 2242205Notes

Reaction equation

HRID 2242205 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:27]=[CH:26][CH:25]=[C:6]([C:7]([NH:9][CH2:10][C@H:11]2[CH2:15][C@@H:14]([C:16]([N:18]3[CH2:22][CH2:21][C:20]([F:24])([F:23])[CH2:19]3)=[O:17])[NH:13][CH2:12]2)=[O:8])[CH:5]=1.FC(F)(F)C(O)=O>CO>[F:24][C:20]1([F:23])[CH2:21][CH2:22][N:18]([C:16]([C@H:14]2[NH:13][CH2:12][C@@H:11]([CH2:10][NH:9][C:7](=[O:8])[C:6]3[CH:5]=[C:4]([CH:27]=[CH:26][CH:25]=3)[C:3]([OH:28])=[O:2])[CH2:15]2)=[O:17])[CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11596365HCID 11596365, compound

Product 1

HCID 11660921HCID 11660921, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Example 72 (58.8 mg) in 0.6 mL of methanol was treated with 1 mL of 1.7 NLiOH solution for 4 hours. Trifluoroacetic acid (300 μL) was added, and the mixture was purified by reverse-phase HPLC to provide the desired acid. MS (ESI) m/z 382 [M+H]+; 1H NMR (500 MHz, methanol-d4) δ ppm 1.57 (ddd, J=19.53, 12.97, 9.61 Hz, 1 H) 2.22 (m, 1 H) 2.32 (m, 1 H) 2.50 (m, 1 H) 2.61 (m, 1 H) 3.02 (dd, J=11.60, 9.15 Hz, 1 H) 3.31 (d, J=6.71 Hz, 2 H) 3.32 (m, 1 H) 3.54 (m, 2 H) 3.66 (m, 2 H) 4.36 (dt, J=41.58, 8.66 Hz, 1 H) 7.38 (t, J=7.78 Hz, 1 H) 7.84 (d, J=8.24 Hz, 1 H) 7.98 (d, J=7.93 Hz, 1 H) 8.28 (m, 1 H).

Workup

  1. customthe mixture was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-7edb7da526ca4064bcfb8967edcfe2d4
Source dataset
uspto-grants-2010_03
Patent number
US07671076B2

Reaction notes

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