Trifluoroacetic acid → HCID 67202348, compound

HRID 1715034Notes

Reaction equation

HRID 1715034 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:14](=[O:15])[C:13]3[CH:16]=[CH:17][CH:18]=[N:19][C:12]=3[N:11]=[C:10]2[C@H:20]([NH:22]C(=O)OC(C)(C)C)[CH3:21])=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:22][C@@H:20]([C:10]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[C:14](=[O:15])[C:13]2[CH:16]=[CH:17][CH:18]=[N:19][C:12]=2[N:11]=1)[CH3:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59465470HCID 59465470, compound

Product 1

HCID 67202348HCID 67202348, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 1 (1.05 g, 2.68 mmol) was dissolved in CH2Cl2 (40 mL) and treated with TFA (40 mL). The resulting mixture was stirred for 1.5 h then concentrated in vacuo. The concentrate was re-dissolved in CH2Cl2 (100 mL) and washed with saturated NaHCO3 (100 mL). The aqueous wash was extracted with additional CH2Cl2 (3×50 mL). The combined extracts were dried over Na2SO4, concentrated and dried under high vacuum for 17 h to give B1 (767 mg, 98%), which was suitable for use without further purification.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe concentrate was re-dissolved in CH2Cl2 (100 mL)
  3. washwashed with saturated NaHCO3 (100 mL)
  4. washThe aqueous wash
  5. extractionwas extracted with additional CH2Cl2 (3×50 mL)
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. concentrationconcentrated
  8. customdried under high vacuum for 17 h

Sources & evidence

ORD record
ord-2abf579098bc4401b5def0625996b034
Source dataset
uspto-grants-2010_09
Patent number
US07799795B2

Reaction notes

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