Trifluoroacetic acid → HCID 178467173, compound

HRID 2089041Notes

Reaction equation

HRID 2089041 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15]C(=O)OC(C)(C)C)[CH2:11][CH2:10]2)[CH:5]=[C:4]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([O:32][CH2:33][CH3:34])[CH:30]=3)[N:25](S(C3C=CC=CC=3)(=O)=O)[CH:24]=2)[CH:3]=1.[OH-].[Na+].C(O)(C(F)(F)F)=O>O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]2)[CH:5]=[C:4]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([O:32][CH2:33][CH3:34])[CH:30]=3)[NH:25][CH:24]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 178467060HCID 178467060, compound

Product 1

HCID 178467173HCID 178467173, compoundYield 13.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of Example 224b (76.1 mg, 0.122 mmol) in dioxane (1.5 mL) was treated with 20% sodium hydroxide (0.10 mL, 0.122 mmol). The mixture was heated at 90° C. for 1 hour. The solvent was evaporated. The residue was treated with 20% brine and extracted with EtOAc (2×). The combined organic layers were dried. The crude intermediate was dissolved in CH2Cl2 (1.0 mL) and treated with TFA (0.19 mL, 2.4 mmol). After 1 hour, the reaction mixture was concentrated and purified by reverse-phase HPLC as described in Example 56 to give the title compound (6.5 mg) as trifluoroacetic acid salts. 1H NMR (400 MHz, CD3OD) ppm 1.29-1.43 (m, 2H), 1.43-1.49 (m, 3H), 1.52-1.72 (m, 2H), 2.02-2.17 (m, 2H), 2.17-2.32 (m, 2H), 3.13 (m, 1H), 3.80 (m, 1H), 4.18 (q, J=7.02 Hz, 2H), 6.75 (d, J=1.22 Hz, 1H), 6.86 (d, J=1.22 Hz, 1H), 7.86 (s, 1H), 7.90 (d, J=2.44 Hz, 1H), 8.06 (d, J=2.44 Hz, 1H). MS (DCI+) m/z 386.2 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. additionThe residue was treated with 20% brine
  3. extractionextracted with EtOAc (2×)
  4. customThe combined organic layers were dried
  5. dissolutionThe crude intermediate was dissolved in CH2Cl2 (1.0 mL)
  6. concentrationthe reaction mixture was concentrated
  7. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-bf4e15e129d54b11b05c2a0fceafc52c
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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