Trifluoroacetic acid → HCID 66741467, compound

HRID 1027896Notes

Reaction equation

HRID 1027896 reaction equation
[N:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2[C:4]([N:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)=[N:3][C:2]=1[N:29]1[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]1.C(O)(C(F)(F)F)=O>>[N:29]1([C:2]2[N:3]=[C:4]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:5]3[CH2:11][CH2:10][CH2:9][C:8]4[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=4[C:6]=3[N:1]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69225949HCID 69225949, compound

Product 1

HCID 66741467HCID 66741467, compound

Conditions

Temperature
60 °C

Procedure

The product from Example 103C (71 mg, 0.13 mmol) was treated with TFA (2 mL), heated at 60° C. for 1 minute, concentrated, dissolved in 1:1 MeOH: CH2Cl2 (2 mL), diluted with CH2Cl2 (25 mL), washed with 1 M NaOH (10 mL) and the layers were separated. The aqueous layer was extracted with CH2Cl2 (25 mL) and the combined organic layers were dried (MgSO4), filtered, concentrated and purified by chromatography on silica gel eluting with 10 and 40% (9:1 MeOH:concentrated NH4OH) in CH2Cl2 to provide the title compound. 1H NMR (CD3OD) δ 2.24-2.40 (m, 4H), 2.65 (t, J=6.5 Hz, 2H), 3.27-3.32 (m, 4H), 3.37-3.42 (m, 4H), 3.66-3.70 (m, 4H), 4.07-4.12 (m, 4H), 7.27-7.31 (m, 1H), 7.32-7.43 (m, 2H), 7.72-7.76 (m, 1H); MS (M+H)+ m/z at 365.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in 1:1 MeOH
  3. additionCH2Cl2 (2 mL), diluted with CH2Cl2 (25 mL)
  4. washwashed with 1 M NaOH (10 mL)
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with CH2Cl2 (25 mL)
  7. dry with materialthe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by chromatography on silica gel eluting with 10 and 40% (9:1 MeOH:concentrated NH4OH) in CH2Cl2

Sources & evidence

ORD record
ord-7746e8756b0a4348bcb2704b299ce4d7
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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