Trifluoroacetic acid → HCID 57635449, compound

HRID 535966Notes

Reaction equation

HRID 535966 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 stiffing, 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-c11a51045aba456b99253765d93f761b
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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