Trifluoroacetic acid → HCID 91665637, compound

HRID 1035321Notes

Reaction equation

HRID 1035321 reaction equation
[CH2:1]([N:8]([CH2:25][C:26]([O:28]CC)=O)[C:9](=[O:24])[C@H:10]([NH:16]C(OC(C)(C)C)=O)[CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:32](F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]1[CH2:25][C:26](=[O:28])[NH:16][C@H:10]([CH2:11][C:12]([O:14][CH2:15][CH3:32])=[O:13])[C:9]1=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67248809HCID 67248809, compound

Product 1

HCID 91665637HCID 91665637, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of Example 255C (50.75 g, 120 mmol) in dichloromethane (50 mL) was added trifluoroacetic acid. The reaction was stirred overnight and then concentrated. Ammonia was added (7 N, methanol, 250 mL) and the solution was warmed to 70° C. for 2 hours. The reaction was concentrated and dichloromethane was added (500 mL). The solution stirred for 10 minutes before the salt was removed by filtration. The solution was then concentrated and purification via flash chromatography (3% 2 N NH3 in methanol/dichloromethane) afforded the title compound.

Workup

  1. concentrationconcentrated
  2. additionAmmonia was added (7 N, methanol, 250 mL)
  3. concentrationThe reaction was concentrated
  4. additiondichloromethane was added (500 mL)
  5. stirringThe solution stirred for 10 minutes before the salt
  6. customwas removed by filtration
  7. concentrationThe solution was then concentrated
  8. custompurification via flash chromatography (3% 2 N NH3 in methanol/dichloromethane)

Sources & evidence

ORD record
ord-eaff4d23406047628cb7089bb2a458f0
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

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