Trifluoroacetic acid → HCID 68720520, compound

HRID 1397483Notes

Reaction equation

HRID 1397483 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][C:6]([C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21]C(=O)OC(C)(C)C)=[C:17]([F:29])[CH:16]=3)=[CH:13][N:14]=2)([OH:9])[CH2:5][CH2:4]1)[CH3:2].FC(F)(F)C(O)=O>ClCCl>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[S:11][C:10]([C:6]3([OH:9])[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]3)=[N:14][CH:13]=2)=[CH:16][C:17]=1[F:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68746268HCID 68746268, compound

Product 1

HCID 68720520HCID 68720520, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ambient solution of Example 8A (0.20 g, 0.48 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (2 mL). The reaction was stirred for 2 h, and was then concentrated under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 (5 mL) and ethyl acetate (5 mL). The layers were separated, and the aqueous was extracted with additional ethyl acetate (2×5 mL). The combined organics were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure to yield the title compound, which was used without further purification. MS (ESI) m/z 322 [M+H]+.

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. customThe residue was partitioned between saturated aqueous NaHCO3 (5 mL) and ethyl acetate (5 mL)
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with additional ethyl acetate (2×5 mL)
  5. dry with materialThe combined organics were dried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-38459a6f1a9f47fc9282f86b89ba0874
Source dataset
uspto-grants-2014_12
Patent number
US08901152B2

Reaction notes

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