Trifluoroacetic acid → HCID 86757104, compound

HRID 1383739Notes

Reaction equation

HRID 1383739 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:15][C:16](=[O:41])[CH:17]([N:21]([C:23](=[O:40])[C@H:24]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[NH:25]C(OC(C)(C)C)=O)[CH3:22])[CH:18]([CH3:20])[CH3:19])[CH3:14])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:15][C:16](=[O:41])[CH:17]([N:21]([CH3:22])[C:23](=[O:40])[C@H:24]([CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[NH2:25])[CH:18]([CH3:20])[CH3:19])[CH3:14])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86757105HCID 86757105, compound

Product 1

HCID 86757104HCID 86757104, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-2-[N-(N-Boc-phenylalanyl)-N-methylamino]-3-methylbutanamide (333 mg) was dissolved in methylene chloride (4 ml) and, after adding TFA (2 ml), the solution was stirred at room temperature for 10 minutes. The solvent was distilled off under reduced pressure and the resulting residue was diluted with methylene chloride and washed with saturated aqueous NaHCO3. The resulting organic layer was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography (eluting solvent consisting of chloroform, methanol and aqueous ammonia at a ratio of 75:1:0.1) to yield N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methyl-2-(N-methyl-N-phenylalanylamino)butanamide in the amount of 164 mg (60%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionthe resulting residue was diluted with methylene chloride
  3. washwashed with saturated aqueous NaHCO3
  4. concentrationThe resulting organic layer was concentrated under reduced pressure
  5. washeluting solvent

Sources & evidence

ORD record
ord-dc672c02a07f4b5cb4b5902da76ca8ad
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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