Trifluoroacetic acid → HCID 117831398, compound

HRID 525313Notes

Reaction equation

HRID 525313 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-ce63434021b14d2ea105c52b46c2e1f0
Source dataset
uspto-grants-2016_05
Patent number
US09340582B2

Reaction notes

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