Hydrogen Bromide → HCID 57440700, compound

HRID 2252644Notes

Reaction equation

HRID 2252644 reaction equation
Br.[CH2:2]([CH:4]1[O:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16]C)[CH:11]=2)[CH2:7][N:6]([CH2:18][CH2:19][CH3:20])[CH2:5]1)[CH3:3]>ClCCl.CO>[CH2:2]([CH:4]1[CH2:5][N:6]([CH2:18][CH2:19][CH3:20])[CH2:7][CH:8]([C:10]2[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=2)[O:9]1)[CH3:3]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 57440699HCID 57440699, compound

Product 1

HCID 57440700HCID 57440700, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Hydrobromic acid (48% aq., 5 mL) and the product from example 46A (0.10 g, 0.38 mmol) were heated at 80° C. for 16 hours. After cooling the reaction mixture was concentrated in vacuo. The residue was partitioned between aqueous ammonia (0.880, 15 mL) and dichloromethane (15 mL), the layers were separated and the aqueous layer re-extracted with dichloromethane (2×15 mL). The organic extracts were combined, dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica eluting with dichloromethane, then dichloromethane:methanol (99:1 to 95:5) to yield the title compound as a clear oil (65 mg, 0.26 mmol, 69%) as the single diastereoisomer. 1H NMR (CDCl3, 400 MHz) δ: 0.95 (m 6H), 1.60 (m, 3H), 1.85 (m, 1H), 2.25 (m, 2H), 2.45 (m, 2H), 2.55 (q, 1H), 2.75 (d, 1H), 3.75 (s, 1H), 4.80 (m, 1H), 6.70 (d, 1H), 6.90 (s, 1H), 7.00 (1H, d), 7.25 (t, 1H). LRMS (APCl): m/z 250 (MH+). Analysis found C, 70.94%; H, 9.16%; N, 5.53%. C15H23NO2.0.3H2O requires C, 70.72%; H, 9.34%; N, 5.50%.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. customThe residue was partitioned between aqueous ammonia (0.880, 15 mL) and dichloromethane (15 mL)
  4. customthe layers were separated
  5. extractionthe aqueous layer re-extracted with dichloromethane (2×15 mL)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography on silica eluting with dichloromethane

Sources & evidence

ORD record
ord-32a31becfe954f27812d020342479088
Source dataset
uspto-grants-2008_01
Patent number
US07323462B2

Reaction notes

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