Hydrochloric Acid → HCID 16203219, compound

HRID 2189963Notes

Reaction equation

HRID 2189963 reaction equation
[C:1]([N:4]1[C@@H:12]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[C@@H:11]2[C:6]([C:7]3[CH:23]=[C:22]([O:24]C)[CH:21]=[CH:20][C:8]=3[CH2:9][CH2:10]2)=[N:5]1)(=[O:3])[CH3:2].B(Br)(Br)Br.Cl>ClCCl>[C:1]([N:4]1[C@@H:12]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[C@@H:11]2[C:6]([C:7]3[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:8]=3[CH2:9][CH2:10]2)=[N:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 16203218HCID 16203218, compound

Product 1

HCID 16203219HCID 16203219, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (175) (0.100 g, 0.28 mmol) under an argon atmosphere in dichloromethane (5 mL) was added BBr3 (1.0 mL, 1.0 M solution in dichloromethane) at −78° C. The reaction mixture was stirred at room temperature for 1 h and then poured into an ice cold solution of HCl (1.0 N). The mixture was extracted in ethyl acetate. The organic layer was washed with water, dried over anhydrous Na2SO4, filtered and concentrated. The solid obtained was recrystallized from ethyl acetate to give (176): (62 mg, 67%): mp 164-67° C., 1H NMR (400 MHz, DMSO-CDCl3): δ 0.70-0.90 (m, 1H), 1.41-1.46 (m, 1H), 2.41-2.57 (m, 5H), 3.15-3.22 (m, 1H), 5.29 (d, J=11.2 Hz, 1H), 6.43 (d, J=6.8 Hz, 2H), 6.53-6.57 (m, 3H), 6.68 (d, J=8.4 Hz, 1H), 7.19 (s, 1H). HFABMS m/z 323.1399 (calc for C19H18N2O3, MH+, 323.1396).

Workup

  1. extractionThe mixture was extracted in ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe solid obtained
  7. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9ed4f7897b634828a84edf67d9d3affe
Source dataset
uspto-grants-2012_12
Patent number
US08324262B2

Reaction notes

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