Trifluoroacetic acid → HCID 69355839, compound

HRID 854367Notes

Reaction equation

HRID 854367 reaction equation
C([O:5][C:6]([C@:8]1([CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:12][C@H:11]([C:13]2[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][N:14]=2)[C@H:10]([C:21]2[S:25][CH:24]=[N:23][CH:22]=2)[N:9]1[C:26](=[O:37])[C:27]1[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[C:33]([C:30]1[CH:29]=[CH:28][C:27]([C:26]([N:9]2[C@@H:10]([C:21]3[S:25][CH:24]=[N:23][CH:22]=3)[C@@H:11]([C:13]3[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][N:14]=3)[CH2:12][C@@:8]2([CH2:38][CH:39]([CH3:40])[CH3:41])[C:6]([OH:7])=[O:5])=[O:37])=[CH:32][CH:31]=1)([CH3:35])([CH3:34])[CH3:36]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69355803HCID 69355803, compound

Product 1

HCID 69355839HCID 69355839, 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-327538600a184897a0d21f9599edd864
Source dataset
uspto-grants-2007_08
Patent number
US07259163B2

Reaction notes

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