Trifluoroacetic acid → HCID 57635449, compound

HRID 1971122Notes

Reaction equation

HRID 1971122 reaction equation
[CH3:1][C:2]([CH3:37])([CH3:36])[C@H:3]([NH:10][C:11]([C:13]1[N:14]=[C:15]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:16]2[CH2:22][CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][C:17]=12)=[O:12])[C:4]1[O:8][N:7]=[C:6]([CH3:9])[N:5]=1.FC(F)(F)C(O)=O>ClCCl.CO>[CH3:1][C:2]([CH3:37])([CH3:36])[C@H:3]([NH:10][C:11]([C:13]1[N:14]=[C:15]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:16]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][C:17]=12)=[O:12])[C:4]1[O:8][N:7]=[C:6]([CH3:9])[N:5]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57635225HCID 57635225, compound

Product 1

HCID 57635449HCID 57635449, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To Compound 517 (219 mg, 0.43 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (1.26 mL, 16.36 mmol). After 3 hours of stirring, the solution was concentrated under reduced pressure. The residue was brought to pH 8 with saturated aqueous NaHCO3. The aqueous solution was extracted twice with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to yield a colorless oil which was dissolved in methanol and loaded onto an ion exchange column (Phenomenex®, SCX). The column was washed with methanol to remove impurities, and the title compound was eluted with a solution of 2N ammonia in methanol. After concentration of the methanol solution, Compound 519 was obtained as a pale yellow solid (148 mg, 84% yield). 1H-NMR (400 MHz, (CD3)2SO) δ: 0.99 (s, 9H), 1.72 (m, 2H), 2.34 (s, 3H), 3.00 (m, 2H), 3.29 (s, 1H), 4.14 (t, 2H), 4.27 (m, 2H), 5.15 (d, 1H), 7.53 (m, 5H), 7.85 (d, 1H). LCMS (+ESI) m/z 409.2 [M+H]+.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. extractionThe aqueous solution was extracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto yield a colorless oil which
  7. washThe column was washed with methanol
  8. customto remove impurities
  9. washthe title compound was eluted with a solution of 2N ammonia in methanol

Sources & evidence

ORD record
ord-56e17308840b4d858a1db5e35ac97473
Source dataset
uspto-grants-2013_04
Patent number
US08431565B2

Reaction notes

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