Hydrogen Bromide → HCID 68615727, compound

HRID 1431978Notes

Reaction equation

HRID 1431978 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]([C:15]#[C:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[BrH:26].C([O-])(O)=O.[Na+].C(OCC)(=O)C>C(Cl)Cl>[Br:26][C:16]1[CH:15]=[C:13]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:17]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 91310653HCID 91310653, compound

Product 1

HCID 68615727HCID 68615727, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

To a stirred solution of 3-(tert-butoxycarbonylamino)-1-propinyl 3,4,5-trimethoxyphenyl ketone (1.0 g, 2.78 mmol, Example 76c) in CH2Cl2 (10 ml) a solution of HBr (732 μl, 1.5 equiv., 33% in acetic acid) is added at 4° C. The reaction mixture is stirred for 45 min at 4° C., and poured onto ice, saturated aqueous NaHCO3 solution and ethyl acetate. The organic layer is dried (MgSO4), the solvents are evaporated and the residue chromatographed on SiO2 with ethyl acetate/hexane (1:3) to yield the title compound (1.0 g, 89.9%) as a white solid. 1H-NMR (300 MHz, DMSO-d6): 7.45 (d, J=2.0, 1H); 6.66 (s, 2H); 6.38 (d, J=2.0, 1H); 3.77 (s, 2MeO); 3.67 (s, MeO); 1.33 (s, tBu).

Workup

  1. dry with materialThe organic layer is dried (MgSO4)
  2. customthe solvents are evaporated
  3. customthe residue chromatographed on SiO2 with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-244ed01315b64de28f4760b786512053
Source dataset
uspto-grants-2009_11
Patent number
US07612064B2

Reaction notes

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