Trifluoroacetic acid → HCID 135520500, compound

HRID 354205Notes

Reaction equation

HRID 354205 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:11]1[CH:12]=[C:13]([C:22]2[NH:23][C:24](=[O:46])[C:25]3[C:26](=[C:28]([CH2:44][CH3:45])[N:29]([CH:31]4[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]4)[N:30]=3)[N:27]=2)[C:14]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[N:15][CH:16]=1)(=[O:10])[CH3:9]>C(Cl)Cl>[C:8]([C:11]1[CH:12]=[C:13]([C:22]2[NH:23][C:24](=[O:46])[C:25]3[C:26](=[C:28]([CH2:44][CH3:45])[N:29]([CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)[N:30]=3)[N:27]=2)[C:14]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[N:15][CH:16]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 135530020HCID 135530020, compound

Product 1

HCID 135520500HCID 135520500, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (7 ml, 40%vol) was added to a solution of the title compound of example 129 in dry Methylene chloride (10 ml), and the mixture was stirred at room temperature under nitrogen for 45 mins. The mixture was concentrated in vacuo and the residue partitioned between NaHCO3 (sat. aq., 50 ml) and Methylene chloride (100 ml). The organic layer was separated (emulsion) and washed with water (50 ml). Organic layer was removed, and the aqueous extracted with Methylene chloride (2×50 ml). The combined organics were dried (MgSO4), and concentrated in vacuo. The crude product was purified by column chromatography (95:5:0.5 methylene chloride:methanol:0.88 NH3 as eluent) to yield the title compound (containing trace impurity; carried through crude to next step).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue partitioned between NaHCO3 (sat. aq., 50 ml) and Methylene chloride (100 ml)
  3. customThe organic layer was separated (emulsion)
  4. washwashed with water (50 ml)
  5. customOrganic layer was removed
  6. extractionthe aqueous extracted with Methylene chloride (2×50 ml)
  7. dry with materialThe combined organics were dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography (95:5:0.5 methylene chloride:methanol:0.88 NH3 as eluent)

Sources & evidence

ORD record
ord-fd9087c4b9f146588a02fee37ff70240
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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