Trifluoroacetic acid → HCID 59639565, compound

HRID 556602Notes

Reaction equation

HRID 556602 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([O:27][CH2:28][CH2:29][NH:30]C(OC(C)(C)C)=O)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:38].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([O:27][CH2:28][CH2:29][NH2:30])[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59639659HCID 59639659, compound

Product 1

HCID 59639565HCID 59639565, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product of Example 130 (1 g, 1.9 mmol) was dissolved in CH2Cl2 (8 mL) and stirred under Ar in an ice bath. A chilled solution of 25% TFA in CH2Cl2 (40 mL) was added, and the mixture was stirred for 45 min at 0° C. The solvents were removed in vacuo, and the residue was partitioned between EtOAc and a saturated NaHCO3 solution. The organic phase was washed with H2O, satd aq NaCl, dried over anhyd Na2SO4, filtered and evaporated to give the crude product. Flash chromatography eluted with 0-10% MeOH/CH2Cl2 gave the title compound as a white-amorphous solid. mp 96-99°, LC MS in/z=427 (MH+) Retention time=1.52 min.

Workup

  1. stirringthe mixture was stirred for 45 min at 0° C
  2. customThe solvents were removed in vacuo
  3. customthe residue was partitioned between EtOAc
  4. washThe organic phase was washed with H2O
  5. dry with materialdried over anhyd Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude product
  9. washFlash chromatography eluted with 0-10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-20755e9faa314c14a22562d02b6948c6
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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