Trifluoroacetic acid → HCID 14186939, compound

HRID 431548Notes

Reaction equation

HRID 431548 reaction equation
C(OC(=O)[NH:7][CH:8]([C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13])[CH:9]([CH3:11])[CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]([CH:9]([CH3:11])[CH3:10])[C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 14186938HCID 14186938, compound

Product 1

HCID 14186939HCID 14186939, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 13 (4.75 g, 12.16 mmol) in CH2Cl2 (10 mL) is added TFA (10 mL). The solution is stirred for 1 h and then quenched with a saturated solution of NaHCO3 (50 mL). The mixture is extracted with CH2Cl2 (50 mL×2). The combined organic layers are washed with 50 mL portions of sat. NaHCO3, water, and brine. It is then dried over Na2SO4 and concentrated to give pure 14 as a yellow oil (3.07 g, 10.56 mmol, 87%). 1H NMR (400 MHz, CDCl3) δ0.87 (t, J=6.8 Hz, 3 H), 0.91 (d, J=6.8, 3 H), 1.65-1.79 (m, 2 H), 1.79-1.96 (m, 2 H), 1.99-2.17 (m, 1 H); 3.27-3.45 (m 1 H), 3.46-3.54 (m, 1 H), 3.59-3.62 (m, 1 H), 4.33-4.38 (m, 1 H), 4.46-4.54 (m, 2 H), 7.27-7.42 (m, 5 H); 13C NMR (100 MHz, CDCl3) δ16.9, 19.8, 24.4, 27.2, 47.2, 56.6, 58.3, 70.1, 73.1, 127.3, 127.4, 128.2, 138.4, 173.8. HRMS calcd for C17H27N2O2 (MH+): 291.2072. Found (DCI): 291.2088 (Δ=−5.3 ppm).

Workup

  1. customquenched with a saturated solution of NaHCO3 (50 mL)
  2. extractionThe mixture is extracted with CH2Cl2 (50 mL×2)
  3. washThe combined organic layers are washed with 50 mL portions of sat. NaHCO3, water, and brine
  4. dry with materialIt is then dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9f371b79a9e048eaacd91b10dd96fa29
Source dataset
uspto-grants-2003_12
Patent number
US06660741B2

Reaction notes

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