Trifluoroacetic anhydride → HCID 178452181, compound

HRID 1361318Notes

Reaction equation

HRID 1361318 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C@H:14]2[CH2:19][CH2:18][C@@H:17]([CH3:20])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:27]([NH2:29])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C@H:14]2[CH2:15][CH2:16][C@@H:17]([CH3:20])[CH2:18][CH2:19]2)[CH2:10][C@H:9]1[C:27]#[N:29])([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 178452182HCID 178452182, compound

Product 1

HCID 178452181HCID 178452181, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of BOC-(2S,4S)-2(aminocarbonyl)-4-[(2,2-dimethylpropanoyl)(cis-4-methylcyclohexyl)amino]pyrrolidine (576 mg, 1.41 mmol) prepared in Step D of Example A7 in DCM (5 ml) was added dropwise TFAA (0.2 ml, 1.41 mmol), and the solution was stirred at rt for 2 h. After the reaction finished, the solution was concentrated in vacuo. The residue was diluted with EtOAc, and washed with brine. The organic solution was dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (eluent: EtOAc:Hex=1/2) to give the title compound (514 mg, 93%).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed with brine
  4. dry with materialThe organic solution was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (eluent: EtOAc:Hex=1/2)

Sources & evidence

ORD record
ord-0cdb7c190ea047588c35066821fef553
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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