Trifluoroacetic acid → HCID 86592305, compound

HRID 1061657Notes

Reaction equation

HRID 1061657 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][NH:10][C:11](=[O:28])[C@@H:12]([NH:20]C(OC(C)(C)C)=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][NH:10][C:11](=[O:28])[C@@H:12]([NH2:20])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21302826HCID 21302826, compound

Product 1

HCID 86592305HCID 86592305, compound

Procedure

Trifluoroacetic acid (4.0 ml) is added to N1-methoxy-(2S)-2-(tert-butoxycarbonyl)amino-3-phenylpropionamide (600 mg, Reference compound No. 22-1), and the mixture is stirred for 10 minutes. The reaction mixture is concentrated under reduced pressure, ethyl acetate is added to the resulting residue, and the whole is extracted with 1 N hydrochloric acid. A saturated sodium hydrogencarbonate solution is added to the extract to basify the system, and the whole is extracted with ethyl acetate. The extract is washed with saturated brine and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure to give the titled reference Compound (70.8 mg).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, ethyl acetate
  2. additionis added to the resulting residue
  3. extractionthe whole is extracted with 1 N hydrochloric acid
  4. additionA saturated sodium hydrogencarbonate solution is added to the
  5. extractionextract
  6. extractionthe whole is extracted with ethyl acetate
  7. washThe extract is washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationThe extract is concentrated under reduced pressure

Sources & evidence

ORD record
ord-400ccf18a0f94daf8b5427d1b985c209
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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