Benzoic Acid → HCID 131720607, compound

HRID 1599106Notes

Reaction equation

HRID 1599106 reaction equation
[ClH:1].[NH2:2][CH2:3][CH2:4][CH2:5][CH:6]([NH:15]C(=O)C1C=CC=CC=1)[CH:7]([OH:14])[C:8]([F:13])([F:12])[CH2:9][CH2:10][CH3:11].C(O)(=O)C1C=CC=CC=1>Cl>[ClH:1].[ClH:1].[NH2:2][CH2:3][CH2:4][CH2:5][CH:6]([NH2:15])[CH:7]([OH:14])[C:8]([F:13])([F:12])[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 131720608HCID 131720608, compound

Product 1

HCID 131720607HCID 131720607, compoundYield 198.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Scheme B, step g (deprotection): Heat to reflux (110° C.) a solution of 9-Amino-6-benzamido-5-hydroxy-4,4-diflurononane, hydrochloride (26.85 g, 76.5 mmol) in conc aq HCl (250 mL) for 19 h. Benzoic acid crystals develop as the reaction mixture is cooled to room temperature. Remove the crystals by filtration. Extract the filtrate with diethyl ether (250 mL) and separate the layers. Treat the aqueous layer with activated carbon, heat (80° C.), filter through celite, concentrate and dry to provide 21.5 g, 75.9 mmol of title compound 1 as a tan solid in quantitative yield. MS (CI, CH4) m/z (% relative intensity) 211 (M+ +1, 43%); 19F NMR (CD3OD) δ (major diastereomer) -106.4 (dt) and -110.6 (m), (minor diastereomer) -107.6 (m) and -112.6 (m), 1H NMR (D2O) δ 4.0, 3.9 (2t, J=4 Hz, 1H, CHCF2), 3.5 (m, 1H, CHN), 2.9 (m, 2H, NCH2), 2.0-1.5 (m, 6H, 3 CH2), 1.3 (m, 2H, CH2), 0.8 (t, J=7 Hz, 3H).

Workup

  1. temperatureScheme B, step g (deprotection): Heat
  2. customRemove the crystals
  3. filtrationby filtration
  4. extractionExtract the filtrate with diethyl ether (250 mL)
  5. customseparate the layers
  6. additionTreat the aqueous layer with activated carbon
  7. temperatureheat (80° C.)
  8. filtrationfilter through celite
  9. concentrationconcentrate
  10. customdry

Sources & evidence

ORD record
ord-0d8d4baf29204236b9c7c501b534df53
Source dataset
uspto-grants-1998_04
Patent number
US05739354

Reaction notes

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