Trifluoroacetic acid → 1-(N-acetyl-L-methionyl)piperazine

HRID 30942Notes

Reaction equation

HRID 30942 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:24])[C@H:15]([CH2:20][CH2:21][S:22][CH3:23])[NH:16][C:17](=[O:19])[CH3:18])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:17]([NH:16][C@H:15]([C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:24])[CH2:20][CH2:21][S:22][CH3:23])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 544692851-(t-butoxycarbonyl)-4(N-acetyl-L-methionyl)piperazine

Product 1

HCID 538025691-(N-acetyl-L-methionyl)piperazineYield 33.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8.6 g (0.024 mol) of 1-(t-butoxycarbonyl) -4-(N-acetyl-L-methionyl)piperazine in 60 ml of dichloromethane was added 10 ml of trifluoroacetic acid and the mixture was stirred at room temperature overnight. The solution was extracted with water and the resulting aqueous solution was made basic with sodium hydroxide. The product was extracted with dichloromethane, dried over sodium sulfate, and filtered. Evaporation of the solvent gave 2.1 g of 1-(N-acetyl-L-methionyl)piperazine, as an oil: IR (film) 3304, 3051, 2917, 2861, 1645, 1546, 1448, 1377 cm−1; NMR (CDCl3) δ 1.95 (m, 2 H), 2.02 (s, 3 H), 2.10 (s, 3 H), 2.54 (m, 2 H), 2.98 (m, 4 H), 3.74 (m, 4 H), 5.10 (m, 1 H), 6.40 (b, 0.5 H), 6.48 (b, 0.5 H).

Workup

  1. extractionThe solution was extracted with water
  2. extractionThe product was extracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-18f8a611ddfa48f4ba3cee9c98a288f7
Source dataset
uspto-grants-2008_09
Patent number
US07425218B2

Reaction notes

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