Sodium Hydroxide → HCID 68505060, compound

HRID 2069456Notes

Reaction equation

HRID 2069456 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4]1[N:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[C:17]([CH2:23][CH3:24])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:25])[N:5]=1)[CH3:2].[OH-].[Na+].Br[CH:31]([OH:33])[CH3:32]>C(O)(C)C.CCOC(C)=O>[CH2:26]([N:3]([CH2:1][CH3:2])[C:4]1[N:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([O:22][CH2:32][CH2:31][OH:33])=[C:17]([CH2:23][CH3:24])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:25])[N:5]=1)[CH3:27]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 14202443Ethanol, 1-bromo-HCID 136339878HCID 136339878, compound

Product 1

HCID 68505060HCID 68505060, compoundYield 105.4%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 11 (1.5 g, 4.08 mmol) in isopropanol (20 mL) is added 3M aq. NaOH (5 mL) followed by bromoethanol (2.90 mL, 40.8 mmol). The reaction mixture is stirred at rt for 15 h, and is then diluted with EtOAc. The org. solution is washed with 1M aq. NaOH followed by brine, dried over Na2SO4, filtered and concentrated. The crude compound is purified by CC (eluting with Heptane/EA 4:1) to give the title compound as a yellow oil (1.77 g); LC-MS: tR=1.16 min; [M+H]+=412.09. 1H NMR (CDCl3) δ1.26 (t, J=7.0 Hz, 6H), 1.33 (t, J=7.5 Hz, 3H), 2.41 (s, 3H), 2.47 (s, 3H), 2.78 (q, J=7.5 Hz, 2H), 2.16 (t, J=5.5 Hz, 1H), 3.76 (q, J=7.0 Hz, 4H), 4.01 (m, 4H), 7.23 (s, 1H), 7.90 (d, J=5.8 Hz, 2H).

Workup

  1. washsolution is washed with 1M aq. NaOH
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude compound is purified by CC (eluting with Heptane/EA 4:1)

Sources & evidence

ORD record
ord-3b4f59b93814461593a1a5939523834e
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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