Hydrochloric Acid → HCID 57448176, compound

HRID 1667585Notes

Reaction equation

HRID 1667585 reaction equation
[CH:1]1([S:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([NH2:10])=O)[CH2:4][CH2:3][CH2:2]1.B.C1COCC1.[ClH:21]>C1COCC1>[ClH:21].[CH:1]1([S:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[CH2:8][NH2:10])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuran2×HCID 57448175HCID 57448175, compound

Product 1

HCID 57448176HCID 57448176, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 2C (5.00 g, 20.9 mmol) in THF (80 mL) at reflux was added a 1M THF solution of BH3.THF (63 mL, 62.7 mmol) via an addition funnel, dropwise over 20 min. After refluxing for 6 h, additional BH3.THF solution was added (20 mL) and refluxing continued overnight. After cooling to rt, 6N HCl (12.5 mL) was added and the reaction was heated again to reflux for 1 h. The reaction was cooled to rt, concentrated then azeotroped (3×) with MeOH/THF. After drying under vacuum for 1 h, the resulting residue was taken up in THF and filtered to provide 2D as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 1.94-2.11 (m, 2H), 2.13-2.26 (m, 2H), 2.43-2.61 (m, 2H), 4.11-4.23 (m, 1H), 4.43 (s, 2H), 7.66-7.76 (m, 2H), 7.81 (t, J=6.81 Hz, 1H), 8.03 (d, J=6.15 Hz, 1H). LC-MS: 226.11 (M+H)+.

Workup

  1. temperatureAfter refluxing for 6 h
  2. temperaturerefluxing continued overnight
  3. temperaturethe reaction was heated again
  4. temperatureto reflux for 1 h
  5. temperatureThe reaction was cooled to rt
  6. concentrationconcentrated
  7. customthen azeotroped (3×) with MeOH/THF
  8. customAfter drying under vacuum for 1 h
  9. filtrationfiltered

Sources & evidence

ORD record
ord-5aad62ff11454ee8a3871abd42954e9e
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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