Trifluoroacetic acid → HCID 86638571, compound

HRID 1807781Notes

Reaction equation

HRID 1807781 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([C:9]1[CH:29]=[CH:28][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][C:15]2=[O:27])=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].FC(F)(F)C(O)=O>ClCCl>[F:30][C:2]([F:1])([F:31])[C:3]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][C:15]2=[O:27])=[CH:28][CH:29]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86638570tert-Butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-3-oxopiperazine-1-carboxylate

Product 1

HCID 86638571HCID 86638571, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-3-oxopiperazine-1-carboxylate (3.05 mmol, 1.39 g) in dichloromethane (15 mL) was added trifluoroacetic acid (30.5 mmol, 3.47 g) and the mixture allowed to stir at room temperature for 5 hours. The reaction mixture was concentrated and the resulting residue purified by strong cation exchange column chromatography to afford the title compound (932 mg). MS (ESI) m/z 357.0 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue purified by strong cation exchange column chromatography

Sources & evidence

ORD record
ord-299ef11c7202411da43f4a4f853779d9
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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