Trifluoroacetic acid → HCID 117831398, compound

HRID 1778644Notes

Reaction equation

HRID 1778644 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][C:13]([C:15]([C:40]([O:42]C(C)(C)C)=[O:41])([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH:38]=[CH2:39])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:14])(C)(C)C>C(Cl)Cl>[CH2:25]([C:26]([OH:28])=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C:15]([C:40]([OH:42])=[O:41])([C:13]([OH:14])=[O:12])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH:38]=[CH2:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117831487HCID 117831487, compound

Product 1

HCID 117831398HCID 117831398, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2 mL) is added to a compound from step 4 (0.022 mmol) and the reaction is stirred at r.t. for 1 hour. The mixture is diluted with DCM (10 mL) and concentrated. The material is taken up in EtOAc (10 mL) and washed with H2O (20 mL). The organic layer is dried over Na2SO4, filtered and concentrated. The crude material is dissolved in 1 mL MeOH and purified via MS-triggered HPLC (Sunfire 30×50 mm 5 um column ACN/H2O w/ 0.1% TFA 75 ml/min, 1.5 ml injection, 45-70% ACN over 3.5 min).

Workup

  1. concentrationconcentrated
  2. washwashed with H2O (20 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe crude material is dissolved in 1 mL MeOH
  7. custompurified via MS-triggered HPLC (Sunfire 30×50 mm 5 um column ACN/H2O w/ 0.1% TFA 75 ml/min, 1.5 ml injection, 45-70% ACN over 3.5 min)

Sources & evidence

ORD record
ord-8b959e8af3da4248bd157b71fab2c7f2
Source dataset
uspto-grants-2016_02
Patent number
US09266925B2

Reaction notes

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