Trifluoroacetic acid → HCID 58158066, compound

HRID 1255518Notes

Reaction equation

HRID 1255518 reaction equation
[CH2:1]([N:5]1[C:14]([O:15][C@H:16]2[CH2:20][N:19](C(OC(C)(C)C)=O)[C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]2)=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:32])[CH2:2][CH:3]=[CH2:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:5]1[C:14]([O:15][C@H:16]2[CH2:20][NH:19][C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]2)=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:32])[CH2:2][CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58157992HCID 58157992, compound

Product 1

HCID 58158066HCID 58158066, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A portion of the product from Step 1 (150 mg, 0.34 mmol) was dissolved in CH2Cl2 (4 ml), cooled in an ice bath, and then added TFA (4 ml). The reaction was allowed to warm to room temperature and stir for 1.5 hours. The reaction was concentrated and the resulting oil was partitioned between CH2Cl2 and sated NaHCO3, extracted with CH2Cl2 (2×), combined organics, washed with brine, dried organics over Na2SO4, filtered, concentrated in vacuo to yield the title compound as a oil (113 mg, 97%). LCMS (ES+) m/z 342.9 (M+H)+.

Workup

  1. temperaturecooled in an ice bath
  2. concentrationThe reaction was concentrated
  3. customthe resulting oil was partitioned between CH2Cl2
  4. extractionextracted with CH2Cl2 (2×)
  5. washwashed with brine, dried organics over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ffc305d294f4dd785e0d0385d53bc70
Source dataset
uspto-grants-2013_06
Patent number
US08461107B2

Reaction notes

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