Trifluoroacetic acid → HCID 54401466, compound

HRID 1737011Notes

Reaction equation

HRID 1737011 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([C@@H:15]1[CH2:20][C@@H:19]([N:21]([CH2:28][C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]=[CH:31][CH:30]=2)C(=O)C(F)(F)F)[CH2:18][CH2:17][N:16]1[C:39](=[O:56])[C@H:40]([CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[NH:41]C(OC(C)(C)C)=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([C@@H:15]1[CH2:20][C@@H:19]([NH:21][CH2:28][C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]=[CH:31][CH:30]=2)[CH2:18][CH2:17][N:16]1[C:39](=[O:56])[C@H:40]([CH2:49][C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)[NH2:41])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57199118HCID 57199118, compound

Product 1

HCID 54401466HCID 54401466, compound

Procedure

3.1 ml (4.09 mmol) of trifluoroacetic acid are added to 920 mg (1.36 mmol) of (2R*,4S*)-2-benzyl-1-((S)-N-tert.-butyloxycarbonyl-phenylalanyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine, and the reaction mixture is stirred at room temperature for 2 hours. It is then concentrated in a rotary evaporator, the residue is taken up in water, basified with 1N sodium bicarbonate solution at 0° C. and extracted with methylene chloride. The organic phases are washed with brine, dried over magnesium sulfate and evaporated to dryness. The residue is chromatographed on silica gel with methylene chloride/methanol/conc. ammonia (2500:50:1) to separate the diastereomers. TLC: methylene chloride/methanol/conc. ammonia (1000:50:1)

Workup

  1. concentrationIt is then concentrated in a rotary evaporator
  2. custombasified with 1N sodium bicarbonate solution at 0° C.
  3. extractionextracted with methylene chloride
  4. washThe organic phases are washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue is chromatographed on silica gel with methylene chloride/methanol/conc
  8. customammonia (2500:50:1) to separate the diastereomers

Sources & evidence

ORD record
ord-5100fa027c464ae680f4ab00d48c024f
Source dataset
uspto-grants-1996_07
Patent number
US05541195

Reaction notes

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