Trifluoroacetic acid → HCID 67517814, compound

HRID 1965212Notes

Reaction equation

HRID 1965212 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[CH:13]2[N:26]([C:29](=[O:43])[CH:30]([NH:35]C(OC(C)(C)C)=O)[C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:27][CH2:28][CH:12]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[CH:13]2[N:26]([C:29](=[O:43])[CH:30]([NH2:35])[C:31]([CH3:32])([CH3:34])[CH3:33])[CH2:27][CH2:28][CH:12]12)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67505722HCID 67505722, compound

Product 1

HCID 67517814HCID 67517814, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of carbamate 81 (542 g, 0.90 mmol) in DCM (10 mL) was treated with TFA (3 mL) at 0° C. After 20 min, the reaction mixture was warmed to ambient temperature. After 1 h, the solution was concentrated, diluted with EtOAc, washed successively with saturated aqueous NaHCO3, and brine, dried over anhydrous Na2SO4, and filtered. The aqueous phase was back-extracted with DCM and the combined organic extracts were concentrated to afford 82 (401 mg, 89%) as a light yellow-colored foam was used without further purification. 1H NMR (CDCl3, 300 MHz): δ7.31-7.26 (m, 5H), 7.00-6.95 (m, 1H), 6.65-6.60 (m, 1H), 6.49-6.47 (m, 1H), 5.14-5.08 (m, 2H), 4.41 (m, 2H), 3.95-3.92 (m, 1H), 3.83-3.72 (m, 2H), 3.40-3.29 (m, 2H), 2.79 (app q, J=5.4 Hz, 1H), 2.34-2.19 (m, 1H), 1.66 (m, 2H), 0.94 (s, 9H) ppm. Mass spectrum, m/z [502.6] (M+H)+.

Workup

  1. waitAfter 1 h
  2. concentrationthe solution was concentrated
  3. additiondiluted with EtOAc
  4. washwashed successively with saturated aqueous NaHCO3, and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. extractionThe aqueous phase was back-extracted with DCM
  8. concentrationthe combined organic extracts were concentrated

Sources & evidence

ORD record
ord-02d69a359f7a4e35834a7e57ff2207d0
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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