Trifluoroacetic acid → HCID 68044577, compound

HRID 1524375Notes

Reaction equation

HRID 1524375 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][CH2:23][CH2:24][CH:25]([F:48])[CH2:26][C@@H:27]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[N:28](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[O:21])[CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][CH2:23][CH2:24][CH:25]([F:48])[CH2:26][C@@H:27]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[NH2:28])=[O:21])[CH:7]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 68044548HCID 68044548, compound

Product 1

HCID 68044577HCID 68044577, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the material from Step 3 (476 mg, 0.706 mmol) in dichloromethane (3 mL) at 0° C. were added anisole (0.232 mL, 2.119 mmol) and TFA (0.653 mL, 8.48 mmol). The reaction mixture was stirred at room temperature for 3 hours, poured into saturated aqueous NaHCO3, and extracted with dichloromethane (2×15 mL). The combined organic layers were dried over MgSO4 and concentrated under vacuum to afford 370 mg of the title compound a colorless foam. LCMS (M+1)=474.

Workup

  1. extractionextracted with dichloromethane (2×15 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9728297b44f349eda9967144a8dda47a
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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