Trifluoroacetic acid → HCID 69355081, compound

HRID 854368Notes

Reaction equation

HRID 854368 reaction equation
[C:1]([C:5]1[CH:39]=[CH:38][C:8]([C:9]([N:11]2[C@@H:15]([C:16]3[S:20][CH:19]=[N:18][CH:17]=3)[C@H:14]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][N:22]=3)[CH2:13][C@@:12]2([CH2:34][CH:35]([CH3:37])[CH3:36])[C:27]([O:29]C(C)(C)C)=[O:28])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([N:11]2[C@@H:15]([C:16]3[S:20][CH:19]=[N:18][CH:17]=3)[C@H:14]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][N:22]=3)[CH2:13][C@@:12]2([CH2:34][CH:35]([CH3:36])[CH3:37])[C:27]([OH:29])=[O:28])=[O:10])=[CH:38][CH:39]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131726562HCID 131726562, compound

Product 1

HCID 69355081HCID 69355081, 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 Supelco ABZ plus column using a gradient of 45-50% acetonitrile/water as the eluent and analysis of the fractions by electrospray mass spectroscopy. The second eluting component was collected and confirmed by nOe studies to be the title compound, isolated as a solid. The first eluted component was the 4-α epimer (Example 56).

Workup

  1. customPurification
  2. customThe second eluting component was collected
  3. customisolated as a solid

Sources & evidence

ORD record
ord-e2b2774b790c456cafdf8a51685bf441
Source dataset
uspto-grants-2007_08
Patent number
US07259163B2

Reaction notes

Loading…