Trifluoroacetic acid → HCID 69286125, compound

HRID 2225292Notes

Reaction equation

HRID 2225292 reaction equation
C(OC([N:8]([CH:38]([CH3:40])[CH3:39])[C@H:9]1[CH2:14][C@@H:13]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[C@@H:12]([NH:21][C:22](=[O:37])[CH2:23][NH:24][C:25](=[O:36])[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:38]([NH:8][C@H:9]1[CH2:14][C@@H:13]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[C@@H:12]([NH:21][C:22](=[O:37])[CH2:23][NH:24][C:25](=[O:36])[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)[CH2:11][CH2:10]1)([CH3:39])[CH3:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86596968HCID 86596968, compound

Product 1

HCID 69286125HCID 69286125, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Step 1 product (120 mg) in CH2Cl2 is treated with CF3COOH (7 ml) and stirred at room temperature for 2 hours. The solution was evaporated and the residue neutralized with 1 N NaOH and extracted into CH2Cl2. The extract was washed with water, brine, dried over Na2SO4, filtered and the solvent evaporated to give 90 mg of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ(TMS): 8.12 (s, 1 H), 8.02 (d, J=7.8 Hz, 1 H), 7.76 (d, J=7.8 Hz, 1 H), 7.57 (t, J=7.8 Hz, 1 H), 7.35 (bt, 1 H), 6.96 (bd, 1 H), 4.93 (m, 1 H), 4.51 (m, 1 H), 4.12 (d, J=4.8 Hz, 2 H), 3.03 (m, 1 H), 2.77 (m, 1 H), 2.61 (m, 1 H), 2.31 (bs, 1 H), 2.04 (m, 2 H), 1.80-1.30 (m, 4 H), 1.17 (m, 6 H), 1.08 (d, J=6.2 Hz, 6 H). MS found: (M+H)+=472.36.

Workup

  1. customThe solution was evaporated
  2. extractionextracted into CH2Cl2
  3. washThe extract was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-4e9b34bbbeb948b89bc61c45dae874d3
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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