Trifluoroacetic acid → HCID 10142859, compound

HRID 854366Notes

Reaction equation

HRID 854366 reaction equation
C([O:5][C:6]([C@:8]1([CH2:39][CH:40]([CH3:42])[CH3:41])[CH2:12][C@H:11]([C:13]2[CH:18]=[N:17][CH:16]=[CH:15][N:14]=2)[C@H:10]([C:19]2[S:23][C:22](Cl)=[N:21][CH:20]=2)[N:9]1[C:25](=[O:38])[C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[C:28]([O:36][CH3:37])[CH:27]=1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[C:32]([C:29]1[CH:30]=[CH:31][C:26]([C:25]([N:9]2[C@@H:10]([C:19]3[S:23][CH:22]=[N:21][CH:20]=3)[C@@H:11]([C:13]3[CH:18]=[N:17][CH:16]=[CH:15][N:14]=3)[CH2:12][C@@:8]2([CH2:39][CH:40]([CH3:41])[CH3:42])[C:6]([OH:7])=[O:5])=[O:38])=[CH:27][C:28]=1[O:36][CH3:37])([CH3:34])([CH3:35])[CH3:33]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69357090HCID 69357090, compound

Product 1

HCID 10142859HCID 10142859, compound

Procedure

The tert-butyl ester from stage A was deprotected with TFA in a similar manner to that described in Example 1. Purification was achieved by reverse phase HPLC on a C18 column using a two-solvent gradient elution with (A) water containing formic acid (0.1%) and (B) acetonitrile-water (95:5 v/v) containing formic acid (0.05%) as the eluents, and analysis of the fractions by electrospray mass spectroscopy. This afforded the title compound as a solid.

Workup

  1. customPurification
  2. washa two-solvent gradient elution with (A) water
  3. additioncontaining formic acid (0.1%) and (B) acetonitrile-water (95:5 v/v)
  4. additioncontaining formic acid (0.05%) as the eluents, and analysis of the fractions by electrospray mass spectroscopy

Sources & evidence

ORD record
ord-8946bfc82f4e4a6996ef536928f3ff24
Source dataset
uspto-grants-2007_08
Patent number
US07259163B2

Reaction notes

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