Acetic Acid → HCID 86660606, compound

HRID 717635Notes

Reaction equation

HRID 717635 reaction equation
[CH2:1]([C:9]1[CH:24]=[CH:23][C:12]([CH:13]=[N:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CC(O)=O>C1COCC1.CCOCC>[CH2:1]([C:9]1[CH:24]=[CH:23][C:12]([CH2:13][NH:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86660607HCID 86660607, compound

Product 1

HCID 86660606HCID 86660606, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step A (0.13 g; 0.391 mmol) in anhydrous THF (1 ml) and glacial AcOH (0.6 ml) NaBH3CN (0.06 g; 0.95 mmol) was added at ˜0° C. (ice bath). The resulting mixture was stirred overnight at room temperature then diluted to 15 ml with Et2O. This was washed with 5% NaHCO3. H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure to give the title compound (0.01 g; 16%) as a colourless syrup, which was used in the next step without further purification. 1H-NMR (CDCl3) 7.23 (d, 2H, J=8 Hz); 7.12 (d, 3H, J=8 Hz); 6.0 (s, 1H); 4.1 (broad s, 2H); 3.94 (s, 2H); 2.57 (t, 3H, J=7.9 Hz); 1.56 (m, 2H); 1.45 (s, 9H); 1.26 (m, 10H); 0.86 (t, 3H, J=7 Hz).

Workup

  1. washThis was washed with 5% NaHCO3
  2. dry with materialH2O, brine, dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-24de365a8e974ee6a039a01fbc728a9a
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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