Acetic Acid → HCID 59000773, compound

HRID 1594018Notes

Reaction equation

HRID 1594018 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:8]([C:27]2[CH:32]=[CH:31][C:30](N)=[CH:29][CH:28]=2)[N:9]2[C:14]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[N:10]2)=[O:5])[CH3:2].C=O.[BH3-][C:42]#[N:43].[Na+].[CH3:45]C(O)=O>CC#N.CCOCC.CCCCCC.CCOCC>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:8]([C:27]2[CH:32]=[CH:31][C:30]([N:43]([CH3:42])[CH3:45])=[CH:29][CH:28]=2)[N:9]2[C:14]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[N:10]2)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 52942491HCID 52942491, compound

Product 1

HCID 59000773HCID 59000773, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 21584099Diethylether hexaneSolvent

Procedure

To a solution of 55 (78 mg, 0.152 mmol) in CH3CN (10 mL) was added 37% aqueous CH2O (123 μL, 1.52 mmol), NaBH3CN (29 mg, 0.450 mmol), and AcOH (31 μL, 0.531 mmol). The reaction mixture was stirred at ambient temperature for 2 h. Et2O was added and the solution was washed with saturated aqueous NaHCO3, brine, dried (MgSO4), filtered, and concentrated in vacuo to provide a yellow oil. Purification by flash chromatography (silica gel, 40% EtOAc/hexane) provided an off-white solid. The solid was suspended in (1:1) Et2O/hexane, collected by vacuum filtration and washed with hexane to provide the title compound as an off-white solid. 1H NMR (DMSO-d6) δ 0.85 (t, J=7.1 Hz, 3H), 1.10 (t, J=7.1 Hz, 3H), 2.96 (s, 6H), 3.40 (m, 4H), 3.51 (q, J=7.2 Hz, 2H), 3.67 (m, 4H), 4.07 (q, J=7.1 Hz, 2H), 6.77 (d, J=9.0 Hz, 2H), 6.82 (s, 1H), 7.44-7.48 (m, 7H). Mass Spectrum (ESI+) m/e=543.2 (M+H).

Workup

  1. washthe solution was washed with saturated aqueous NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a yellow oil
  6. customPurification by flash chromatography (silica gel, 40% EtOAc/hexane)
  7. customprovided an off-white solid
  8. filtrationcollected by vacuum filtration
  9. washwashed with hexane

Sources & evidence

ORD record
ord-9c009ca08b374ff3bea9547fefd9d0fd
Source dataset
uspto-grants-2007_11
Patent number
US07300932B2

Reaction notes

Loading…