Trifluoroacetic acid → HCID 44184100, compound

HRID 451327Notes

Reaction equation

HRID 451327 reaction equation
C(O)(C(F)(F)F)=O.[O:8]=[C:9]1[N:15]2[CH2:16][C@@H:11]([CH2:12][CH2:13][C@H:14]2[C:17]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)=[O:18])[N:10]1[O:34][S:35]([OH:38])(=[O:37])=[O:36]>>[O:8]=[C:9]1[N:15]2[CH2:16][C@@H:11]([CH2:12][CH2:13][C@H:14]2[C:17]([O:19][CH2:20][CH:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)=[O:18])[N:10]1[O:34][S:35]([OH:38])(=[O:37])=[O:36]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86659600HCID 86659600, compound

Product 1

HCID 44184100HCID 44184100, compound

Procedure

TFA was added to the product of Step 3 at 0° C. under nitrogen. The reaction mixture was stirred for 1 hour then concentrated under vacuum. The residue was triturated with ether to remove excess trifluoroacetic acid and organic-soluble impurities. The resulting solid was dried, dissolved in water, and purified by preparative HPLC on a Phenomenex Synergy Polar-RP 80A column eluted with methanol/water and lyophilized to afford the title compound. LC-MS (negative ionization mode) m/e 362 (M−H).

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe residue was triturated with ether
  3. customto remove excess trifluoroacetic acid and organic-soluble impurities
  4. customThe resulting solid was dried
  5. dissolutiondissolved in water
  6. custompurified by preparative HPLC on a Phenomenex Synergy Polar-RP 80A column
  7. washeluted with methanol/water

Sources & evidence

ORD record
ord-ed05e86d51724602bdbdb6438ccc3637
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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