Trifluoroacetic acid → HCID 69943705, compound

HRID 744881Notes

Reaction equation

HRID 744881 reaction equation
COC1C=CC(COC([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:36])[C@@H:18]([OH:35])[CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)=[O:23])[CH2:13][CH2:12]2)=O)=CC=1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[N+:32]([C:29]1[CH:28]=[CH:27][C:26]([CH2:25][O:24][C:22]([NH:21][CH2:20][CH2:19][C@H:18]([OH:35])[C:17]([N:14]2[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]2)=[O:36])=[O:23])=[CH:31][CH:30]=1)([O-:34])=[O:33]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 69943109HCID 69943109, compound

Product 1

HCID 69943705HCID 69943705, compoundYield 99.8%

Procedure

A 1.32 g of 1-(p-methoxybenzyloxycarbonyl)-4-((2S)-4-(p-nitrobenzyloxycarbonyl) amino-2-hydroxybutyryl)piperazine was added to a mixture of 15 ml of trifluoroacetic acid and 1.35 ml of anisole, followed by 1 hour of reaction at room temperature. After removing trifluoroacetic acid by evaporation under a reduced pressure, a residue was adjusted to basic with sodium hydroxide and extracted with chloroform, and the organic layer was washed with water and dried over sodium sulfate, followed by evaporation of the solvent under a reduced pressure. Thereafter, the resulting residue was subjected to a silica gel column chromatography to yield 0.91 g of 1-((2S)-4-(p-nitrobenzyloxycarbonyl)amino-2-hydroxybutyryl)piperazine as a syrup.

Workup

  1. customfollowed by 1 hour of reaction at room temperature
  2. customAfter removing trifluoroacetic acid
  3. customby evaporation under a reduced pressure
  4. extractionextracted with chloroform
  5. washthe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customfollowed by evaporation of the solvent under a reduced pressure

Sources & evidence

ORD record
ord-018824ab7c844e9db8785c5138c5f1f5
Source dataset
uspto-grants-1996_09
Patent number
US05559224

Reaction notes

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