Trifluoroacetic acid → 1-[2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-2-one

HRID 1466063Notes

Reaction equation

HRID 1466063 reaction equation
[OH:1][CH:2]([C:18]1[CH:27]=[CH:26][C:21]2[C:22](=[O:25])[O:23][CH2:24][C:20]=2[C:19]=1[CH3:28])[CH2:3][N:4]1[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][C:5]1=[O:17].C(O)(C(F)(F)F)=O>>[OH:1][CH:2]([C:18]1[CH:27]=[CH:26][C:21]2[C:22](=[O:25])[O:23][CH2:24][C:20]=2[C:19]=1[CH3:28])[CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][C:5]1=[O:17]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89526106tert-Butyl 4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-3-oxopiperazine-1-carboxylate

Product 1

HCID 895334841-[2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-2-one

Procedure

The product of Step A was treated with TFA to remove the Boc group. The crude material was dissolved in aqueous sodium bicarbonate, extracted with Chloroform-IPA (3:1) three times, dried over sodium sulfate and concentrated to furnish the title compound (free base). LC-MS (IE, m/z): 291 [M+1]+.

Workup

  1. customto remove the Boc group
  2. dissolutionThe crude material was dissolved in aqueous sodium bicarbonate
  3. extractionextracted with Chloroform-IPA (3:1) three times
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e666cff72e1b417eb21cece2e1cc2110
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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