Trifluoroacetic acid → HCID 86680331, compound

HRID 2360708Notes

Reaction equation

HRID 2360708 reaction equation
COC(=O)[C@H:4]([N:7]([C:17](=[O:28])[C@@H:18]([NH:20][C:21](OC(C)(C)C)=[O:22])[CH3:19])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[CH2:5][CH3:6].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:5]([C@H:4]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:17](=[O:28])[C@H:18]([CH3:19])[NH:20][C:21]1=[O:22])[CH3:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86680332HCID 86680332, compound

Product 1

HCID 86680331HCID 86680331, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.60 g of (R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-(4-methoxy-benzyl)-amino]-butyric acid methyl ester in 116 ml DCM were added 116 ml of TFA at 0° C. during 1 h. After 2 h at 0° C. the reaction mixture was allowed to come to r.t. and stirred for another 1.5 h. The reaction mixture was then concentrated in vacuo, dissolved in EtOAc, and 120 ml of 1M aqueous NaHCO3-solution were added. After stirring for 1 h, the layers were separated. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 5.34 g (100%) of the title compound, which was used without further purification.

Workup

  1. customto come to r.t.
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. dissolutiondissolved in EtOAc
  4. addition120 ml of 1M aqueous NaHCO3-solution were added
  5. stirringAfter stirring for 1 h
  6. customthe layers were separated
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ca909f256a64867b65ba182709a5c12
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

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