Trifluoroacetic acid → Benzyl piperazine-1-carboxylate

HRID 1518752Notes

Reaction equation

HRID 1518752 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14](C(=O)COC[C@@H](C)[C@H](N(C(OC(C)(C)C)=O)C)C2OC=CC=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86718357HCID 86718357, compound

Product 1

HCID 643495Benzyl piperazine-1-carboxylateYield 160.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-{2-[(2S,3S)-3-(tert-butoxycarbonyl-methylamino)-3-furan-2-yl-2-methyl-propoxy]-acetyl}-piperazine-1-carboxylic acid benzyl ester (250.0 mg, 0.47 mmol) in DCM (4 mL) at 0° C. was added TFA (4 mL). After stirring for 1 hour, the reaction mixture was diluted with DCM (30 mL) and washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 4-[2-(2S,3S)-3-furan-2-yl-2-methyl-3-methylamino-propoxy)-acetyl]-piperazine-1-carboxylic acid benzyl ester as a solid (166.0 mg) which was used for the next step without further purification. MS m/z (M+1) 430.3

Workup

  1. washwashed with saturated aqueous NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c0571ce65ad34b23aa05497302258100
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

Loading…