Trifluoroacetic acid methylene chloride → Trifluoroacetic acid

HRID 79127Notes

Reaction equation

HRID 79127 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[N:21]=[N:20][C:19]([N:22]5[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)=[CH:18][CH:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:35]=[CH:36][NH:37][C:38](=[O:39])[C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41].C(Cl)Cl>>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[N:21]=[N:20][C:19]([N:22]5[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]5)=[CH:18][CH:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:35]=[CH:36][NH:37][C:38](=[O:39])[C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1.[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 58299615HCID 58299615, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 58300013HCID 58300013, compound

Procedure

Compound 162 was treated with 1:1 TFA/DCM (2 mL) at room temperature for an hour. The solvent was evaporated. The residue was re-dissolved in 4 mLl methanol and purified on a C-18 reverse phase column (150×30 mm, 4 micro) using Mass directed preparative HPLC and gradient elution of acetonitrile in water containing 0.1% TFA to provide the title compound 161 as a TFA salt. LCMS retention time (minutes): 0.793. LCMS-ESI (POS), M/Z, M+1: 432.2

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was re-dissolved in 4 mLl methanol
  3. custompurified on a C-18 reverse phase column (150×30 mm, 4 micro)
  4. washHPLC and gradient elution of acetonitrile in water containing 0.1% TFA

Sources & evidence

ORD record
ord-5aaffe191f3f49f59db22d38e654414f
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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