Trifluoroacetic acid → HCID 67202348, compound

HRID 547583Notes

Reaction equation

HRID 547583 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, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 16 (1.05 g, 2.68 mmol), prepared as described in Section 7.12, 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 P1 (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
  9. customto give P1 (767 mg, 98%), which
  10. customwas suitable for use without further purification

Sources & evidence

ORD record
ord-558a9fec849943499f88822f27af5e9a
Source dataset
uspto-grants-2011_05
Patent number
US07939538B2

Reaction notes

Loading…