Trifluoroacetic acid → HCID 69151595, compound

HRID 1744165Notes

Reaction equation

HRID 1744165 reaction equation
[CH3:1][C@@H:2]1[CH2:6][N:5](C(OC(C)(C)C)=O)[C@H:4]([C:14]([O:16]C(C)(C)C)=[O:15])[CH2:3]1.[C:21]([OH:27])([C:23]([F:26])([F:25])[F:24])=[O:22]>C(Cl)Cl>[F:24][C:23]([F:26])([F:25])[C:21]([OH:27])=[O:22].[CH3:1][C@@H:2]1[CH2:6][NH:5][C@H:4]([C:14]([OH:16])=[O:15])[CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69152992HCID 69152992, compound

Product 1

HCID 69151595HCID 69151595, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To di(tert-butyl) (2S,4S)-4-methylpyrrolidine-1,2-dicarboxylate (Ref: J. Amer. Chem. Soc., 1996, 118, 36, 8700–8706, 2.4 g, 8.42 mmol) in CH2Cl2 (15 mL) was added TFA (15 mL) and the reaction was stirred for 2 hours. The reaction was concentrated in vacuo and re-dissolved in CH2Cl2 (15 mL), TFA (15 mL) was added and the reaction was stirred for 1 hour. The reaction was concentrated in vacuo to afford (4S)-4-methyl-L-proline trifluoroacetate and used directly in the next step.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionre-dissolved in CH2Cl2 (15 mL)
  3. additionTFA (15 mL) was added
  4. stirringthe reaction was stirred for 1 hour
  5. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-4d3191e277d043bcaab4485359cea940
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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