Trifluoroacetic acid → HCID 10277581, compound

HRID 854365Notes

Reaction equation

HRID 854365 reaction equation
[C:1]([C:5]1[CH:37]=[CH:36][C:8]([C:9]([N:11]2[C@@H:15]([CH:16]([CH3:18])[CH3:17])[C@@H:14]([C:19]3[CH:24]=[N:23][CH:22]=[CH:21][N:20]=3)[CH2:13][C@@:12]2([CH2:32][CH:33]([CH3:35])[CH3:34])[C:25]([O:27]C(C)(C)C)=[O:26])=[O:10])=[CH:7][C:6]=1[O:38][CH3:39])([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>>[C:1]([C:5]1[CH:37]=[CH:36][C:8]([C:9]([N:11]2[C@@H:15]([CH:16]([CH3:18])[CH3:17])[C@@H:14]([C:19]3[CH:24]=[N:23][CH:22]=[CH:21][N:20]=3)[CH2:13][C@@:12]2([CH2:32][CH:33]([CH3:34])[CH3:35])[C:25]([OH:27])=[O:26])=[O:10])=[CH:7][C:6]=1[O:38][CH3:39])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131726561HCID 131726561, compound

Product 1

HCID 10277581HCID 10277581, 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-2227ec9990f545a8b26482e437c10860
Source dataset
uspto-grants-2007_08
Patent number
US07259163B2

Reaction notes

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