Trifluoroacetic acid → (3R,6S)-1-(4-Fluoro-benzyl)-3,6-dimethyl-piperazine-2,5-dione

HRID 11607Notes

Reaction equation

HRID 11607 reaction equation
CO[C:3](=O)[C@@H:4]([N:6]([C:15](=[O:26])[C@H:16]([NH:18][C:19](OC(C)(C)C)=[O:20])[CH3:17])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)C.FC(F)(F)C(O)=O>ClCCl>[F:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][N:6]2[C@@H:4]([CH3:3])[C:19](=[O:20])[NH:18][C@H:16]([CH3:17])[C:15]2=[O:26])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57016912(2S)-2-[(2R)-(2-Tert-Butoxycarbonylamino-Propionyl)-(4-Fluoro-Benzyl)-Amino]propionic Acid Methyl Ester

Product 1

HCID 69325248(3R,6S)-1-(4-Fluoro-benzyl)-3,6-dimethyl-piperazine-2,5-dioneYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-2-[(2R)-(2-tert-butoxycarbonylamino-propionyl)-(4-fluoro-benzyl)-amino]-propionic acid methyl ester (43 g, 382 mmol) in dichloromethane (120 mL) at 0° C. was added trifluoroacetic acid (60 mL). The reaction was allowed to warm to ambient temperature and stirred for 2 hours. The reaction was cooled to 0° C. and slowly quenched by addition of 3 N sodium hydroxide until basic. The resulting mixture was extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound (22 g).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customslowly quenched by addition of 3 N sodium hydroxide until basic
  3. extractionThe resulting mixture was extracted with dichloromethane
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c843a15b5d714641a5db49ffbd9018c2
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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