Acetic Acid → HCID 178495830, compound

HRID 1631442Notes

Reaction equation

HRID 1631442 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([NH:17][NH2:18])=O)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26]OC(OC)N(C)C.[CH3:34][O:35][CH2:36][CH2:37][NH2:38].C(O)(=O)C>O.C1COCC1.C(#N)C>[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]2[N:38]([CH2:37][CH2:36][O:35][CH3:34])[CH:26]=[N:18][N:17]=2)[CH2:13][CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 178514427HCID 178514427, compound

Product 1

HCID 178495830HCID 178495830, compoundYield 83.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

14A (300 mg, 0.889 mmol) was treated with acetonitrile (2 mL) and THF (0.5 mL). This clear solution was treated with N,N-dimethylformamide dimethylacetal (0.30 mL, 2.22 mmol) and the reaction mixture was stirred at 50° C. for 45 min. The mixture was treated with 2-methoxyethanamine (0.230 mL, 2.67 mmol) resulting in a yellow clear solution. Acetic acid (0.5 mL, 8.73 mmol) was added, and the reaction was stirred at 90° C. overnight. The reaction was diluted with water and extracted with 25% MeOH in dichloromethane (3×). The combined organic extracts were washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by Isco silica column (12 g), (gradient elution with methanol-dichloromethane over 12 min.) Concentration of the appropriate fractions provided 14B (300 mg, 0.742 mmol, 83% yield) as a pale yellow oil. MS (ES): m/z=405.2 [M+H]+.

Workup

  1. customresulting in a yellow clear solution
  2. stirringthe reaction was stirred at 90° C. overnight
  3. extractionextracted with 25% MeOH in dichloromethane (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by Isco silica column (12 g), (gradient elution with methanol-dichloromethane over 12 min.) Concentration of the appropriate fractions

Sources & evidence

ORD record
ord-6888a6e3004f44d0ac9ac2621106d03b
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

Loading…