Trifluoroacetic acid → HCID 22120220, compound

HRID 1400960Notes

Reaction equation

HRID 1400960 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:20])([CH3:19])[CH2:5][N:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:19][C:4]([CH3:20])([CH2:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)[C:3]([O:2][CH3:1])=[O:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68155978Tert-butyl 4-(3-methoxy-2,2-dimethyl-3-oxopropyl)piperazine-1-carboxylate

Product 1

HCID 22120220HCID 22120220, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 568 (1.137 g, 3.79 mmol) and TFA (15 ml) in DCM (30 ml) was stirred at rt for 2.5 h. The reaction mixture was concentrated (azeotropes with DCM), diluted with water, stirred for 1 h, and the pH was adjusted to around 9-10 with 1N NaOH. The alkaline solution was extracted with DCM. The extract was dried over anhydrous magnesium sulfate, filtered, concentrated and dried under high vacuum to afford the desired product 569 (667 mg, 3.33 mmol, 88% yield) as a pale-yellow viscous liquid. The crude material was used in the next step without any further purification. MS (z): 201.1 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated (azeotropes with DCM)
  2. additiondiluted with water
  3. extractionThe alkaline solution was extracted with DCM
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-d61d432d32874c2ea8beb27b80862d84
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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